This invention relates to plant fatty acyl hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acyl hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fattyacids in transgenic plants. In addition, the use of genes encoding fattyacid hydroxylases or desaturases to alter the level of lipid fattyacid unsaturation in transgenic plants is described.

In one aspect, a radioactively labeled analog of a fattyacid which is capable of being taken up by mammalian tissue and which exhibits an in vivo beta-oxidation rate below that with a corresponding radioactively labeled fattyacid.

OBJECTIVE To examine evidence for the role of omega-3 fattyacids in cardiovascular disease. QUALITY OF EVIDENCE PubMed was searched for articles on the role of omega-3 fattyacids in cardiovascular disease. Level I and II evidence indicates that omega-3 fattyacids are beneficial in improving cardiovascular outcomes. MAIN MESSAGE Dietary intake of omega-3 fattyacids has declined by 80% during the last 100 years, while intake of omega-6 fattyacids has greatly increased. Omega-3 fattyacids are cardioprotective mainly due to beneficial effects on arrhythmias, atherosclerosis, inflammation, and thrombosis. There is also evidence that they improve endothelial function, lower blood pressure, and significantly lower triglycerides. CONCLUSION There is good evidence in the literature that increasing intake of omega-3 fattyacids improves cardiac outcomes. Physicians need to integrate dietary recommendations for consumption of omega-3 fattyacids into their usual cardiovascular care. PMID:16812965

Omega-6 fattyacids are types of fats. Some types are found in vegetable oils, including corn, evening primrose seed, safflower, and soybean oils. Other types of omega-6 fattyacids are found in black currant seed, borage seed, ...

Omega-3 fattyacids are used together with lifestyle changes (diet, weight-loss, exercise) to reduce the amount of triglycerides (a fat-like ... people with very high triglycerides. Omega-3 fattyacids are in a class of medications called antilipemic ...

The present invention relates to a method for producing mutants of a fattyacid desaturase having a substantially increased activity towards fattyacid substrates with chains containing fewer than 18 carbons relative to an unmutagenized precursor desaturase having an 18 carbon atom chain length substrate specificity. The method involves inducing one or more mutations in the nucleic acid sequence encoding the precursor desaturase, transforming the mutated sequence into an unsaturated fattyacid auxotroph cell such as MH13 E. coli, culturing the cells in the absence of supplemental unsaturated fattyacids, thereby selecting for recipient cells which have received and which express a mutant fattyacid desaturase with an elevated specificity for fattyacid substrates having chain lengths of less than 18 carbon atoms. A variety of mutants having 16 or fewer carbon atom chain length substrate specificities are produced by this method. Mutant desaturases produced by this method can be introduced via expression vectors into prokaryotic and eukaryotic cells and can also be used in the production of transgenic plants which may be used to produce specific fattyacid products.

Fats and their various fattyacid components seem to be a perennial concern of nutritionists and persons concerned with healthful diets. Advice on the consumption of saturated, polyunsaturated, monounsaturated, and total fat bombards us from magazines and newspapers. One of the newer players in this field is the group of trans fattyacids found predominantly in partially hydrogenated fats such as margarines and cooking fats. The controversy concerning dietary trans fattyacids was recently addressed in an American Heart Association (AHA) science advisory (1) and in a position paper from the American Society of Clinical Nutrition/American Institute of Nutrition (ASCN/AIN) (2). Both reports emphasize that the best preventive strategy for reducing risk for cardiovascular disease and some types of cancer is a reduction in total and saturated fats in the diet, but a reduction in the intake of trans fattyacids was also recommended. Although the actual health effects of trans fattyacids remain uncertain, experimental evidence indicates that consumption of trans fattyacids adversely affects serum lipid levels. Since elevated levels of serum cholesterol and triacylglycerols are associated with increased risk of cardiovascular disease, it follows that intake of trans fattyacids should be minimized.

Dietary fat was recognized as a good source of energy and fat-soluble vitamins by the first part of the 20th century, but fattyacids were not considered to be essential nutrients because they could be synthesized from dietary carbohydrate. This well-established view was challenged in 1929 by George and Mildred Burr who reported that dietary fattyacid was required to prevent a deficiency disease that occurred in rats fed a fat-free diet. They concluded that fattyacids were essential nutrients and showed that linoleic acid prevented the disease and is an essential fattyacid. The Burrs surmised that other unsaturated fattyacids were essential and subsequently demonstrated that linolenic acid, the omega-3 fattyacid analog of linoleic acid, is also an essential fattyacid. The discovery of essential fattyacids was a paradigm-changing finding, and it is now considered to be one of the landmark discoveries in lipid research. PMID:25339684

Described are hosts for overproducing a fattyacid product such as a fattyacid. The hosts include an exogenous nucleic acid encoding a thioesterase and, optionally, an exogenous nucleic acid encoding an acetyl-CoA carboxylase, wherein an acyl-CoA synthetase in the hosts are functionally delected. The hosts prefereably include the nucleic acid encoding the thioesterase at an intermediate copy number. The hosts are preferably recominantly stable and growth-competent at 37.degree. C. Methods of producing a fattyacid product comprising culturing such hosts at 37.degree. C. are also described.

Polyunsaturated fattyacids (PUFAs) are considered to be critical nutrients to regulate human health and development, and numerous fattyacid desaturases play key roles in synthesizing PUFAs. Given the lack of delta-12 and -15 desaturases and the low levels of conversion to PUFAs, humans must consume some omega-3 and omega-6 fattyacids in their diet. Many studies on fattyacid desaturases as well as PUFAs have shown that fattyacid desaturase genes are closely related to different human physiological conditions. Since the first front-end desaturases from cyanobacteria were cloned, numerous desaturase genes have been identified and animals and plants have been genetically engineered to produce PUFAs such as eicosapentaenoic acid and docosahexaenoic acid. Recently, a biotechnological approach has been used to develop clinical treatments for human physiological conditions, including cancers and neurogenetic disorders. Thus, understanding the functions and regulation of PUFAs associated with human health and development by using biotechnology may facilitate the engineering of more advanced PUFA production and provide new insights into the complexity of fattyacid metabolism. PMID:26742061

Polyunsaturated fattyacids (PUFAs) are considered to be critical nutrients to regulate human health and development, and numerous fattyacid desaturases play key roles in synthesizing PUFAs. Given the lack of delta-12 and -15 desaturases and the low levels of conversion to PUFAs, humans must consume some omega-3 and omega-6 fattyacids in their diet. Many studies on fattyacid desaturases as well as PUFAs have shown that fattyacid desaturase genes are closely related to different human physiological conditions. Since the first front-end desaturases from cyanobacteria were cloned, numerous desaturase genes have been identified and animals and plants have been genetically engineered to produce PUFAs such as eicosapentaenoic acid and docosahexaenoic acid. Recently, a biotechnological approach has been used to develop clinical treatments for human physiological conditions, including cancers and neurogenetic disorders. Thus, understanding the functions and regulation of PUFAs associated with human health and development by using biotechnology may facilitate the engineering of more advanced PUFA production and provide new insights into the complexity of fattyacid metabolism.

The immune system acts to protect the host against pathogenic invaders. However, components of the immune system can become dysregulated such that their activities are directed against host tissues, so causing damage. Lymphocytes are involved in both the beneficial and detrimental effects of the immune system. Both the level of fat and the types of fattyacid present in the diet can affect lymphocyte functions. The fattyacid composition of lymphocytes, and other immune cells, is altered according to the fattyacid composition of the diet and this alters the capacity of those cells to produce eicosanoids, such as prostaglandin E2, which are involved in immunoregulation. A high fat diet can impair lymphocyte function. Cell culture and animal feeding studies indicate that oleic, linoleic, conjugated linoleic, gamma-linolenic, dihomo-gamma-linolenic, arachidonic, alpha-linolenic, eicosapentaenoic and docosahexaenoic acids can all influence lymphocyte proliferation, the production of cytokines by lymphocytes, and natural killer cell activity. High intakes of some of these fattyacids are necessary to induce these effects. Among these fattyacids the long chain n-3 fattyacids, especially eicosapentaenoic acid, appear to be the most potent when included in the human diet. Although not all studies agree, it appears that fish oil, which contains eicosapentaenoic acid, down regulates the T-helper 1-type response which is associated with chronic inflammatory disease. There is evidence for beneficial effects of fish oil in such diseases; this evidence is strongest for rheumatoid arthritis. Since n-3 fattyacids also antagonise the production of inflammatory eicosanoid mediators from arachidonic acid, there is potential for benefit in asthma and related diseases. Recent evidence indicates that fish oil may be of benefit in some asthmatics but not others.

The formation of fattyacids by Fischer-Tropsch-type synthesis was investigated with ferric oxide, ammonium carbonate, potassium carbonate, powdered Pueblito de Allende carbonaceous chondrite, and filings from the Canyon Diablo meteorite used as catalysts. Products were separated and identified by gas chromatography and mass spectrometry. Iron oxide, Pueblito de Allende chondrite, and Canyon Diablo filings in an oxidized catalyst form yielded no fattyacids. Canyon Diablo filings heated overnight at 500 C while undergoing slow purging by deuterium produced fattyacids only when potassium carbonate was admixed; potassium carbonate alone also produced these compounds. The active catalytic combinations gave relatively high yields of aliphatic and aromatic hydrocarbons; substantial amounts of n-alkenes were almost invariably observed when fattyacids were produced; the latter were in the range C6 to C18, with maximum yield in C9 or 10.

The present invention relates to the identification of nucleic acid sequences and constructs, and methods related thereto, and the use of these sequences and constructs to produce genetically modified plants for the purpose of altering the composition of plant oils, waxes and related compounds.

All organisms that produce fattyacids do so via a repeated cycle of reactions. In mammals and other animals, these reactions are catalyzed by a type I fattyacid synthase (FAS), a large multifunctional protein to which the growing chain is covalently attached. In contrast, most bacteria (and plants) contain a type II system in which each reaction is catalyzed by a discrete protein. The pathway of fattyacid biosynthesis in Escherichia coli is well established and has provided a foundation for elucidating the type II FAS pathways in other bacteria (White et al., 2005). However, fattyacid biosynthesis is more diverse in the phylum Actinobacteria: Mycobacterium, possess both FAS systems while Streptomyces species have only the multi-enzyme FAS II system and Corynebacterium species exclusively FAS I. In this review we present an overview of the genome organization, biochemical properties and physiological relevance of the two FAS systems in the three genera of actinomycetes mentioned above. We also address in detail the biochemical and structural properties of the acyl-CoA carboxylases (ACCases) that catalyzes the first committed step of fattyacid synthesis in actinomycetes, and discuss the molecular bases of their substrate specificity and the structure-based identification of new ACCase inhibitors with anti-mycobacterial properties. PMID:21204864

Fifty brands of margarine were analysed for cis-polyunsaturated acids by lipoxidase, for trans fattyacid by infared spectroscopy, and for fattyacid composition by gas-liquid chromatography. High concentrations of trans fattyacids tended to be associated with low concentrations of linoleic acid. Later analyses on eight of the brands, respresenting various proportions of linoleic to trans fattyacids, indicated that two of them contained still higher levels of trans fattyacids (greater than 60%) and negligible amounts of linoleic acid. It is proposed that margarine could be a vehicle for the distribution of some dietary linoleic acid and that the level of linoleic acid and the summation of the saturated plus trans fattyacids be known to ascertain nutritional characteristics.

Nonalcoholic fatty liver disease (NAFLD) is characterized by fat deposition in hepatocytes, and a strong association with nutritional factors. Dietary fattyacids are classified according to their biochemical properties, which confer their bioactive roles. Monounsaturated fattyacids have a dual role in various human and murine models. In contrast, polyunsaturated fattyacids exhibit antiobesity, anti steatosic and anti-inflammatory effects. The combination of these forms of fattyacids-according to dietary type, daily intake and the proportion of n-6 to n-3 fats-can compromise hepatic lipid metabolism. A chemosensory rather than a nutritional role makes bioactive fattyacids possible biomarkers for NAFLD. Bioactive fattyacids provide health benefits through modification of fattyacid composition and modulating the activity of liver cells during liver fibrosis. More and better evidence is necessary to elucidate the role of bioactive fattyacids in nutritional and clinical treatment strategies for patients with NAFLD.

The cellular fattyacid composition of 14 strains of Caulobacter speices and types, two species of Prosthecomicrobium, and two species of Asticcacaulis was determined by gas-liquid chromatography. In most of these bacteria, the major fattyacids were octadecenoic acid (C18:1), hexadecenoic acid (C16:1) and hexadecanoic acid (C16:0). Some cyclopropane and branched chain fattyacids were detected in addition to the straight chained acids. Hydroxytetradecanoic acid was an important component of P.enhydrum but significant amounts of hydroxy acids were not detected in other prosthecate bacteria examined.

OMEGA-3 FATTYACIDS DURING PREGNANCY S HARE W ITH W OMEN OMEGA-3 FATTYACIDS DURING PREGNANCY During pregnancy, your baby gets most ... eat and vitamins you take. Omega-3 fattyacids (omega-3s) are an important family of building ...

Nitrated fattyacids are the product of nitrogen dioxide reaction with unsaturated fattyacids. The discovery of peroxynitrite and peroxidase-induced nitration of biomolecules led to the initial reports of endogenous nitrated fattyacids. These species increase during ischemia/reperfusion, but concentrations are often at or near the limits of detection. Here, we describe multiple methods for nitrated fattyacid synthesis and sample extraction from complex biological matrices and a rigorous method of qualitative and quantitative detection of nitrated fattyacids by liquid chromatography-mass spectrometry. In addition, optimized instrument conditions and caveats regarding data interpretation are discussed.

Nitrated fattyacids are the product of nitrogen dioxide reaction with unsaturated fattyacids. The discovery of peroxynitrite and peroxidase-induced nitration of biomolecules led to the initial reports of endogenous nitrated fattyacids. These species increase during ischemia reperfusion, but concentrations are often at or near the limits of detection. Here, we describe multiple methods for nitrated fattyacid synthesis, sample extraction from complex biological matrices, and a rigorous method of qualitative and quantitative detection of nitrated fattyacids by LC-MS. In addition, optimized instrument conditions and caveats regarding data interpretation are discussed. PMID:23200809

Radiolabeled long-chain fattyacids have diagnostic value as radiopharmaceutical tools in myocardial imaging. Some applications of these fattyacids are limited due to their natural metabolic degradation in vivo with subsequent washout of the radioactivity from the myocardium. The identification of structural features that will increase the myocardial residence time without decreasing the heart uptake of long-chain fattyacids is of interest. Fattyacids containing the tellurium heteroatom were the first modified fattyacids developed that show unique prolonged myocardial retention and low blood levels. Our detailed studies with radioiodinated vinyliodide substituted tellurium fattyacids demonstrate that heart uptake is a function of the tellurium position. New techniques of tellurium and organoborane chemistry have been developed for the synthesis of a variety of radioiodinated iodoalkenyl tellurium fattyacids. 9 refs., 3 figs., 2 tabs.

Dietary saturated fattyacids containing 12- to 18-carbon atoms satisfy growth requirements of Neurospora crassa mutant cel (previously named ol; Perkins et al., reference 11); unsaturated fattyacids are synthesized by direct desaturation when an appropriate saturate is available. Odd-chain saturates, 15 carbons and 17 carbons long, satisfy the requirement, and elaidic acid (18:1 Δ9trans) results in slow growth. Oleic acid and other cis-unsaturated fattyacids do not satisfy growth requirements; however, oleic acid plus elaidic acid result in growth at a faster rate than elaidate alone. The use of a spin-label fattyacid reveals that hyphae produced by cel during a slow basal level of growth have lipids that reflect a relatively rigid state of viscosity compared to wild type. cel Supplemented with fattyacids and wild type supplemented in the same way have lipids of the same viscosities as reflected by electron spin resonance. PMID:4323964

The metabolic effects of salicylates are poorly understood. This study investigated the effects of aspirin on fattyacid oxidation. Aspirin increased mitochondrial long-chain fattyacid oxidation, but inhibited peroxisomal fattyacid oxidation, in two different cell lines. Aspirin increased mitochondrial protein acetylation and was found to be a stronger acetylating agent in vitro than acetyl-CoA. However, aspirin-induced acetylation did not alter the activity of fattyacid oxidation proteins, and knocking out the mitochondrial deacetylase SIRT3 did not affect the induction of long-chain fattyacid oxidation by aspirin. Aspirin did not change oxidation of medium-chain fattyacids, which can freely traverse the mitochondrial membrane. Together, these data indicate that aspirin does not directly alter mitochondrial matrix fattyacid oxidation enzymes, but most likely exerts its effects at the level of long-chain fattyacid transport into mitochondria. The drive on mitochondrial fattyacid oxidation may be a compensatory response to altered mitochondrial morphology and inhibited electron transport chain function, both of which were observed after 24 h incubation of cells with aspirin. These studies provide insight into the pathophysiology of Reye Syndrome, which is known to be triggered by aspirin ingestion in patients with fattyacid oxidation disorders.

Epidemiological evidence suggests that dietary consumption of the long chain omega-3 fattyacids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), commonly found in fish or fish oil, may modify the risk for certain neuropsychiatric disorders. As evidence, decreased blood levels of omega-3 fattyacids have been associated with several neuropsychiatric conditions, including Attention Deficit (Hyperactivity) Disorder, Alzheimer's Disease, Schizophrenia and Depression. Supplementation studies, using individual or combination omega-3 fattyacids, suggest the possibility for decreased symptoms associated with some of these conditions. Thus far, however, the benefits of supplementation, in terms of decreasing disease risk and/or aiding in symptom management, are not clear and more research is needed. The reasons for blood fattyacid alterations in these disorders are not known, nor are the potential mechanisms by which omega-3 fattyacids may function in normal neuronal activity and neuropsychiatric disease prevention and/or treatment. It is clear, however, that DHA is the predominant n-3 fattyacid found in the brain and that EPA plays an important role as an anti-inflammatory precursor. Both DHA and EPA can be linked with many aspects of neural function, including neurotransmission, membrane fluidity, ion channel and enzyme regulation and gene expression. This review summarizes the knowledge in terms of dietary omega-3 fattyacid intake and metabolism, as well as evidence pointing to potential mechanisms of omega-3 fattyacids in normal brain functioning, development of neuropsychiatric disorders and efficacy of omega-3 fattyacid supplementation in terms of symptom management.

The fattyacid profile of kenaf (Hibiscus cannabinus L.) seed oil has been the subject of several previous reports in the literature. These reports vary considerably regarding the presence and amounts of specific fattyacids, notably epoxyoleic acid but also cyclic (cyclopropene and cyclopropane) fa...

Bile acids are known to play important roles as detergents in the absorption of hydrophobic nutrients and as signaling molecules in the regulation of metabolism. Here we tested the novel hypothesis that naturally occurring bile acids interfere with protein-mediated hepatic long chain free fattyacid (LCFA) uptake. To this end stable cell lines expressing fattyacid transporters as well as primary hepatocytes from mouse and human livers were incubated with primary and secondary bile acids to determine their effects on LCFA uptake rates. We identified ursodeoxycholic acid (UDCA) and deoxycholic acid (DCA) as the two most potent inhibitors of the liver-specific fattyacid transport protein 5 (FATP5). Both UDCA and DCA were able to inhibit LCFA uptake by primary hepatocytes in a FATP5-dependent manner. Subsequently, mice were treated with these secondary bile acids in vivo to assess their ability to inhibit diet-induced hepatic triglyceride accumulation. Administration of DCA in vivo via injection or as part of a high-fat diet significantly inhibited hepatic fattyacid uptake and reduced liver triglycerides by more than 50%. In summary, the data demonstrate a novel role for specific bile acids, and the secondary bile acid DCA in particular, in the regulation of hepatic LCFA uptake. The results illuminate a previously unappreciated means by which specific bile acids, such as UDCA and DCA, can impact hepatic triglyceride metabolism and may lead to novel approaches to combat obesity-associated fatty liver disease. PMID:22531947

The total fatty constituents of slash pine (Pinus elliottii) tissue cultures, seeds, and seedlings were examined by GLC and MS. Qualitatively, the fattyacid composition of these tissues was found to be very similar to that reported for other pine species. The fattyacid contents of the tissue cultures resembled that of the seedling tissues. The branched-chain C(sub 17) acid reported for several other Pinus species was confirmed as the anteiso isomer.

Low concentrations of branched-chain fattyacids, such as isobutyric and isovaleric acids, develop during the ripening of hard cheeses and contribute to the beneficial flavor profile. Catabolism of amino acids, such as branched-chain amino acids, by bacteria via aminotransferase reactions and alpha-keto acids is one mechanism to generate these flavorful compounds; however, metabolism of alpha-keto acids to flavor-associated compounds is controversial. The objective of this study was to determine the ability of Brevibacterium linens BL2 to produce fattyacids from amino acids and alpha-keto acids and determine the occurrence of the likely genes in the draft genome sequence. BL2 catabolized amino acids to fattyacids only under carbohydrate starvation conditions. The primary fattyacid end products from leucine were isovaleric acid, acetic acid, and propionic acid. In contrast, logarithmic-phase cells of BL2 produced fattyacids from alpha-keto acids only. BL2 also converted alpha-keto acids to branched-chain fattyacids after carbohydrate starvation was achieved. At least 100 genes are potentially involved in five different metabolic pathways. The genome of B. linens ATCC 9174 contained these genes for production and degradation of fattyacids. These data indicate that brevibacteria have the ability to produce fattyacids from amino and alpha-keto acids and that carbon metabolism is important in regulating this event.

Essential fattyacids (EFA) are nutrients that form an amazingly large array of bioactive mediators that act on a large family of selective receptors. Nearly every cell and tissue in the human body expresses at least one of these receptors, allowing EFA-based signaling to influence nearly every aspect of human physiology. In this way, the health consequences of specific gene-environment interactions with these nutrients are more extensive than often recognized. The metabolic transformations have similar competitive dynamics for the n-3 and n-6 homologs when converting dietary EFA from the external environment of foods into the highly unsaturated fattyacid (HUFA) esters that accumulate in the internal environment of cells and tissues. In contrast, the formation and action of bioactive mediators during tissue responses to stimuli tend to selectively create more intense consequences for n-6 than n-3 homologs. Both n-3 and n-6 nutrients have beneficial actions, but many common health disorders are undesired consequences of excessive actions of tissue n-6 HUFA which are preventable. This review considers the possibility of preventing imbalances in dietary n-3 and n-6 nutrients with informed voluntary food choices. That action may prevent the unintended consequences that come from eating imbalanced diets which support excessive chronic actions of n-6 mediators that harm human health. The consequences from preventing n-3 and n-6 nutrient imbalances on a nationwide scale may be very large, and they need careful evaluation and implementation to avoid further harmful consequences for the national economy. PMID:23112921

Nickel exposure is associated with changes in cellular energy metabolism which may contribute to its carcinogenic properties. Here, we demonstrate that nickel strongly represses mitochondrial fattyacid oxidation-the pathway by which fattyacids are catabolized for energy-in both primary human lung fibroblasts and mouse embryonic fibroblasts. At the concentrations used, nickel suppresses fattyacid oxidation without globally suppressing mitochondrial function as evidenced by increased glucose oxidation to CO2. Pre-treatment with l-carnitine, previously shown to prevent nickel-induced mitochondrial dysfunction in neuroblastoma cells, did not prevent the inhibition of fattyacid oxidation. The effect of nickel on fattyacid oxidation occurred only with prolonged exposure (>5 h), suggesting that direct inhibition of the active sites of metabolic enzymes is not the mechanism of action. Nickel is a known hypoxia-mimetic that activates hypoxia inducible factor-1α (HIF1α). Nickel-induced inhibition of fattyacid oxidation was blunted in HIF1α knockout fibroblasts, implicating HIF1α as one contributor to the mechanism. Additionally, nickel down-regulated the protein levels of the key fattyacid oxidation enzyme very long-chain acyl-CoA dehydrogenase (VLCAD) in a dose-dependent fashion. In conclusion, inhibition of fattyacid oxidation by nickel, concurrent with increased glucose metabolism, represents a form of metabolic reprogramming that may contribute to nickel-induced carcinogenesis.

In the search of value-added products from surplus soybean oil, we produced many new hydroxy fattyacids through microbial bioconversion. Hydroxy fattyacids are used in a wide range of industrial products, such as resins, waxes, nylons plastics, lubricants, cosmetics, and additives in coatings and...

Nickel exposure is associated with changes in cellular energy metabolism which may contribute to its carcinogenic properties. Here, we demonstrate that nickel strongly represses mitochondrial fattyacid oxidation—the pathway by which fattyacids are catabolized for energy—in both primary human lung fibroblasts and mouse embryonic fibroblasts. At the concentrations used, nickel suppresses fattyacid oxidation without globally suppressing mitochondrial function as evidenced by increased glucose oxidation to CO2. Pre-treatment with L-carnitine, previously shown to prevent nickel-induced mitochondrial dysfunction in neuroblastoma cells, did not prevent the inhibition of fattyacid oxidation. The effect of nickel on fattyacid oxidation occurred only with prolonged exposure (>5 hr), suggesting that direct inhibition of the active sites of metabolic enzymes is not the mechanism of action. Nickel is a known hypoxia-mimetic that activates hypoxia inducible factor-1α (HIF1α). Nickel-induced inhibition of fattyacid oxidation was blunted in HIF1α knockout fibroblasts, implicating HIF1α as one contributor to the mechanism. Additionally, nickel down-regulated the protein levels of the key fattyacid oxidation enzyme very long-chain acyl-CoA dehydrogenase (VLCAD) in a dose-dependent fashion. In conclusion, inhibition of fattyacid oxidation by nickel, concurrent with increased glucose metabolism, represents a form of metabolic reprogramming that may contribute to nickel-induced carcinogenesis. PMID:26051273

Fattyacids are basic renewable chemical building blocks that can be used as intermediates for a multitude of products. Today the global value of fattyacids exceeds 18 billion dollars and is expected to increase to nearly 26 billion over the period from 2014-2019. From it auspicious beginnings, the...

Free fattyacids of human skin surface lipids have previously been implicated in the pathogenesis of acne vulgaris because of their apparent irritant and comedogenic properties. Prior studies on the relative irritancy of free fattyacids revealed the saturated C8 to C14 fattyacids and a C18 dienoic unsaturated fattyacid (linoleic) to be most irritating. Saturated free fattyacids from C3 to C18, and unsaturated C18 free fattyacids were applied daily under occlusive patch tests to human skin until detectable erythema appeared. The most irritating fattyacids were C8 through C12. Of the unsaturated fattyacids tested, only linoleic acid produced irritation.

Cardioceuticals are nutritional supplements that contain all the essential nutrients including vitamins, minerals, omega-3-fattyacids and other antioxidants like a-lipoic acid and coenzyme Q10 in the right proportion that provide all round protection to the heart by reducing the most common risks associated with the cardiovascular disease including high low-density lipoprotein cholesterol and triglyceride levels and factors that contribute to coagulation of blood. Omega-3 fattyacids have been shown to significantly reduce the risk for sudden death caused by cardiac arrhythmias and all-cause mortality in patients with known coronary heart disease. Omega-3 fattyacids are also used to treat hyperlipidemia and hypertension. There are no significant drug interactions with omega-3 fattyacids. The American Heart Association recommends consumption of two servings of fish per week for persons with no history of coronary heart disease and at least one serving of fish daily for those with known coronary heart disease. Approximately 1 g/day of eicosapentaenoic acid plus docosahexaenoic acid is recommended for cardio protection. Higher dosages of omega-3 fattyacids are required to reduce elevated triglyceride levels (2-4 g/day). Modest decreases in blood pressure occur with significantly higher dosages of omega-3 fattyacids.

A fundamental feature of the life history of true seals, bears and baleen whales is lactation while fasting. This study examined the mobilization of fattyacids from blubber and their subsequent partitioning into maternal metabolism and milk production in northern elephant seals (Mirounga angustirostris). The fattyacid composition of blubber and milk was measured in both early and late lactation. Proportions of fattyacids in milk and blubber were found to display a high degree of similarity both early and late in lactation. Seals mobilized an enormous amount of lipid (~66 kg in 17 days), but thermoregulatory fattyacids, those that remain fluid at low temperatures, were relatively conserved in the outer blubber layer. Despite the stratification, the pattern of mobilization of specific fattyacids conforms to biochemical predictions. Long chain (>20C) monounsaturated fattyacids (MUFAs) were the least mobilized from blubber and the only class of fattyacids that showed a proportional increase in milk in late lactation. Polyunsaturated fattyacids (PUFAs) and saturated fattyacids (SFAs) were more mobilized from the blubber, but neither proportion increased in milk at late lactation. These data suggest that of the long chain MUFA mobilized, the majority is directed to milk synthesis. The mother may preferentially use PUFA and SFA for her own metabolism, decreasing the availability for deposition into milk. The potential impacts of milk fattyacid delivery on pup diving development and thermoregulation are exciting avenues for exploration.

Degradation of unusual fattyacids through β-oxidation within transgenic plants has long been hypothesized as a major factor limiting the production of industrially useful unusual fattyacids in seed oils. Arabidopsis seeds expressing the castor fattyacid hydroxylase accumulate hydroxylated fattyacids up to 17% of total fattyacids in seed triacylglycerols; however, total seed oil is also reduced up to 50%. Investigations into the cause of the reduced oil phenotype through in vivo [14C]acetate and [3H]2O metabolic labeling of developing seeds surprisingly revealed that the rate of de novo fattyacid synthesis within the transgenic seeds was approximately half that of control seeds. RNAseq analysis indicated no changes in expression of fattyacid synthesis genes in hydroxylase-expressing plants. However, differential [14C]acetate and [14C]malonate metabolic labeling of hydroxylase-expressing seeds indicated the in vivo acetyl–CoA carboxylase activity was reduced to approximately half that of control seeds. Therefore, the reduction of oil content in the transgenic seeds is consistent with reduced de novo fattyacid synthesis in the plastid rather than fattyacid degradation. Intriguingly, the coexpression of triacylglycerol synthesis isozymes from castor along with the fattyacid hydroxylase alleviated the reduced acetyl–CoA carboxylase activity, restored the rate of fattyacid synthesis, and the accumulation of seed oil was substantially recovered. Together these results suggest a previously unidentified mechanism that detects inefficient utilization of unusual fattyacids within the endoplasmic reticulum and activates an endogenous pathway for posttranslational reduction of fattyacid synthesis within the plastid. PMID:24398521

Analyses of two carbonaceous meteorites have provided much of the latest evidence which seems to support Oparin's theory on the origin of life. The meteorites involved are the Murray meteorite, which fell in 1950, and the Murchison meteorite, which fell in 1969. The amino acids in the two meteorites are similar in composition. Eight of the twenty amino acids found belong to amino acids present in proteins. A number of monocarboxylic and dicarboxylic fattyacids were also found in the meteorites.

Cystic fibrosis patients and model systems exhibit consistent abnormalities in metabolism of polyunsaturated fattyacids that appear to play a role in disease pathophysiology. Recent in vitro studies have suggested that these changes are due to overexpression of fattyacid desaturases that can be reversed by supplementation with the long-chain polyunsaturated fattyacids docosahexaenoate and eicosapentaenoate. However, these findings have not been tested in vivo. The current study aimed to test these results in an in vivo model system, the CFTR(-/-) knockout mouse. When compared with wild-type mice, the knockout mice exhibited fattyacid abnormalities similar to those seen in cystic fibrosis patients and other model systems. The abnormalities were confined to lung, ileum and pancreas, tissues that are affected by the disease. Similar to in vitro models, these fattyacid changes correlated with increased expression of Δ5- and Δ6-desaturases and elongase 5. Dietary supplementation with high-dose free docosahexaenoate or a combination of lower-dose docosahexaenoate and eicosapentaenoate in triglyceride form corrected the fattyacid abnormalities and reduced expression of the desaturase and elongase genes in the ileum and liver of knockout mice. Only the high-dose docosahexaenoate reduced histologic evidence of disease, reducing mucus accumulation in ileal sections. These results provide in vivo support for the hypothesis that fattyacid abnormalities in cystic fibrosis result from abnormal expression and activity of metabolic enzymes in affected cell types. They further demonstrate that these changes can be reversed by dietary n-3 fattyacid supplementation, highlighting the potential therapeutic benefit for cystic fibrosis patients.

Fattyacid amino acid conjugates (FACs) have been found in Noctuid as well as Sphingid caterpillar oral secretions and especially volicitin [N-(17-hydroxylinolenoyl)-L-Glutamine] and its biochemical precursor, N-linolenoyl-L-glutamine, are known elicitors of induced volatile emissions in corn plants...

The health benefits of fish oil have been known for decades. Most of the health benefits of fish oil can be attributed to the presence of omega-3 essential fattyacids such as docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA). Clinical studies have suggested that DHA and EPA lower triglycerides; slow the buildup of atherosclerotic plaques; lower blood pressure slightly; as well as reduce the risk of death, heart attack, and arrhythmias. Studies have also shown that omega-3 fattyacids may slow the progression of vision loss from AMD and reverse the signs of dry eye syndrome.

The purpose of this article is to describe the structure, function and metabolism of fattyacids and lipids that are of particular importance in the context of parenteral nutrition. Lipids are a heterogeneous group of molecules that share the common property of hydrophobicity. Lipids range in structure from simple short hydrocarbon chains to more complex molecules, including triacylglycerols, phospholipids and sterols and their esters. Lipids within each class may differ structurally. Fattyacids are common components of complex lipids, and these differ according to chain length and the presence, number and position of double bonds in the hydrocarbon chain. Structural variation among complex lipids and among fattyacids gives rise to functional differences that result in different impacts upon metabolism and upon cell and tissue responses. Fattyacids and complex lipids exhibit a variety of structural variations that influence their metabolism and their functional effects.

Astrocytes were derived from cortex of two-day-old rat brain and grown in primary culture to confluence. The metabolism of the fattyacids, octanoate and palmitate, to CO{sub 2} in oxidative respiration and to the formation of ketone bodies was examined by radiolabeled tracer methodology. The net production of acetoacetate was also determined by measurement of its mass. The enzymes in the ketogenic pathway were examined by measuring enzymic activity and/or by immunoblot analyses. Labeled CO{sub 2} and labeled ketone bodies were produced from the oxidation of fattyacids labeled at carboxy- and {omega}-terminal carbons, indicating that fattyacids were oxidized by {beta}-oxidation. The results from the radiolabeled tracer studies also indicated that a substantial proportion of the {omega}-terminal 4-carbon unit of the fattyacids bypassed the {beta}-ketothiolase step of the {beta}-oxidation pathway. The ({sup 14}C)acetoacetate formed from the (1-{sup 14}C)labeled fattyacids, obligated to pass through the acetyl-CoA pool, contained 50% of the label at carbon 3 and 50% at carbon 1. In contrast, the ({sup 14}C)acetoacetate formed from the ({omega}-1)labeled fattyacids contained 90% of the label at carbon 3 and 10% at carbon 1.

A physiological relationship between iron, oxidative injury, and fattyacid metabolism exists, but transduction mechanisms are unclear. We propose that the iron storage protein ferritin contains fattyacid binding sites whose occupancy modulates iron uptake and release. Using isothermal microcalorimetry, we found that arachidonic acid binds ferritin specifically and with 60 μM affinity. Arachidonate binding by ferritin enhanced iron mineralization, decreased iron release, and protected the fattyacid from oxidation. Cocrystals of arachidonic acid and horse spleen apoferritin diffracted to 2.18 Å and revealed specific binding to the 2-fold intersubunit pocket. This pocket shields most of the fattyacid and its double bonds from solvent but allows the arachidonate tail to project well into the ferrihydrite mineralization site on the ferritin L-subunit, a structural feature that we implicate in the effects on mineralization by demonstrating that the much shorter saturated fattyacid, caprylate, has no significant effects on mineralization. These combined effects of arachidonate binding by ferritin are expected to lower both intracellular free iron and free arachidonate, thereby providing a previously unrecognized mechanism for limiting lipid peroxidation, free radical damage, and proinflammatory cascades during times of cellular stress.

Lactobacillus plantarum AKU 1009a effectively transforms linoleic acid to conjugated linoleic acids of cis-9,trans-11-octadecadienoic acid (18:2) and trans-9,trans-11-18:2. The transformation of various polyunsaturated fattyacids by washed cells of L. plantarum AKU 1009a was investigated. Besides linoleic acid, alpha-linolenic acid [cis-9,cis-12,cis-15-octadecatrienoic acid (18:3)], gamma-linolenic acid (cis-6,cis-9,cis-12-18:3), columbinic acid (trans-5,cis-9,cis-12-18:3), and stearidonic acid [cis-6,cis-9,cis-12,cis-15-octadecatetraenoic acid (18:4)] were found to be transformed. The fattyacids transformed by the strain had the common structure of a C18 fattyacid with the cis-9,cis-12 diene system. Three major fattyacids were produced from alpha-linolenic acid, which were identified as cis-9,trans-11,cis-15-18:3, trans-9,trans-11,cis-15-18:3, and trans-10,cis-15-18:2. Four major fattyacids were produced from gamma-linolenic acid, which were identified as cis-6,cis-9,trans-11-18:3, cis-6,trans-9,trans-11-18:3, cis-6,trans-10-18:2, and trans-10-octadecenoic acid. The strain transformed the cis-9,cis-12 diene system of C18 fattyacids into conjugated diene systems of cis-9,trans-11 and trans-9,trans-11. These conjugated dienes were further saturated into the trans-10 monoene system by the strain. The results provide valuable information for understanding the pathway of biohydrogenation by anaerobic bacteria and for establishing microbial processes for the practical production of conjugated fattyacids, especially those produced from alpha-linolenic acid and gamma-linolenic acid.

A light particle fraction of Saccharomyces cerevisiae, obtained from the crude ribosomal material, and containing the fattyacid synthetase, consisted primarily of 27S and 47S components. This fraction has a protein-ribonucleic acid ratio of about 13. Electron micrographs showed particles ranging in diameter between 100 and 300 A in this material. By use of density gradient analysis, the fattyacid synthetase was found in the 47S component. This component contained particles which were predominantly 300 A in diameter and which were considerably flatter than ribosomes, and it consisted almost entirely of protein. Images PMID:6025308

Although it is known that the fattyacid profile of human milk is altered by diet, the rapidity with which this occurs has not been addressed. We hypothesized that after absorption the fattyacids of a given meal would be transferred rapidly from the chylomicrons of the blood into human milk. Fourteen lactating women drank six test formulas, each containing a different fat: menhaden oil, herring oil, safflower oil, canola oil, coconut oil, or cocoa butter. The subjects collected a midfeeding milk sample before consuming the breakfast test formula and additional samples at 6, 10, 14, and 24 h and then once daily for 4-7 d. Fattyacids of special interest included eicosapentaenoic and docosahexaenoic acids from menhaden oil, cetoleic acid from herring oil, linoleic acid from safflower oil, linolenic acid from canola oil, lauric acid from coconut oil, and palmitic and stearic acids from cocoa butter. Each of these fattyacids increased significantly in human milk within 6 h of consumption of the test formulas (P < 0.001). Maximum increases occurred 10 h after safflower oil; 14 h after cocoa utter, coconut oil, canola oil, and menhaden oil (eicosapentaenoic acid); and 24 h after herring oil and menhaden oil (docosahexaenoic acid). All of these fattyacids remained significantly elevated in milk (P < 0.05) for 10-24 h, except for docosahexaenoic acid, which remained significantly elevated for 2 d, and eicosapentaenoic acid, which remained elevated for 3 d. These data support the hypothesis that there is a rapid transfer of dietary fattyacids from chylomicrons into human milk.

The fattyacids of six wild edible mushroom species (Boletus reticulatus, Flammulina velutipes var. velutipes, Lactarius salmonicolor, Pleurotus ostreatus, Polyporus squamosus, and Russula anthracina) collected from different regions from Anatolia were determined. The fattyacids were identified and quantified by gas chromatography and studied using fruit bodies. Fattyacid composition varied among species. The dominant fattyacid in fruit bodies of all mushrooms was cis-linoleic acid (18 : 2). Percentage of cis-linoleic acid in species varied from 22.39% to 65.29%. The other major fattyacids were, respectively, cis-oleic, palmitic, and stearic acids. Fattyacids analysis of the mushrooms showed that the unsaturated fattyacids were at higher concentrations than saturated fattyacids. PMID:23844377

Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fattyacid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having unsaturated esters.

The uptake and metabolism of long chain fattyacids (LCFA) are critical to many physiological and cellular processes. Aberrant accumulation or depletion of LCFA underlie the pathology of numerous metabolic diseases. Protein-mediated transport of LCFA has been proposed as the major mode of LCFA uptake and activation. Several proteins have been identified to be involved in LCFA uptake. This review focuses on the SLC27 family of fattyacid transport proteins, also known as FATPs, with an emphasis on the gain- and loss-of-function animal models that elucidate the functions of FATPs in vivo and how these transport proteins play a role in physiological and pathological situations.

In both eukaryotes and prokaryotes, fattyacid synthases are responsible for the biosynthesis of fattyacids in an iterative process, extending the fattyacid by two carbon units every cycle. Thus, odd numbered fattyacids are rarely found in nature. We tested whether representatives of diverse microbial phyla have the ability to incorporate odd-chain fattyacids as substrates for their fattyacid synthases and their downstream enzymes. We fed various odd and short chain fattyacids to the bacterium Escherichia coli, cyanobacterium Synechocystis sp. PCC 6803, green microalga Chlamydomonas reinhardtii and diatom Thalassiosira pseudonana. Major differences were observed, specifically in the ability among species to incorporate and elongate short chain fattyacids. We demonstrate that E. coli, C. reinhardtii, and T. pseudonana can produce longer fattyacid products from short chain precursors (C3 and C5), while Synechocystis sp. PCC 6803 lacks this ability. However, Synechocystis can incorporate and elongate longer chain fattyacids due to acyl-acyl carrier protein synthetase (AasS) activity, and knockout of this protein eliminates the ability to incorporate these fattyacids. In addition, expression of a characterized AasS from Vibrio harveyii confers a similar capability to E. coli. The ability to desaturate exogenously added fattyacids was only observed in Synechocystis and C. reinhardtii. We further probed fattyacid metabolism of these organisms by feeding desaturase inhibitors to test the specificity of long-chain fattyacid desaturases. In particular, supplementation with thia fattyacids can alter fattyacid profiles based on the location of the sulfur in the chain. We show that coupling sensitive gas chromatography mass spectrometry to supplementation of unnatural fattyacids can reveal major differences between fattyacid metabolism in various organisms. Often unnatural fattyacids have antibacterial or even therapeutic properties. Feeding of short

Eight almond (Prunus dulcis L.) cultivars from 12 different California counties, collected during crop years 2004 to 2005 and 2005 to 2006, were extracted with petroleum ether. The extracts were subjected to GC-MS analyses to determine fattyacid composition of soluble lipids. Results indicated palmitic (C16:0), oleic (C18:1), linoleic (C18:2), and alpha-linolenic (C18:3) acid, respectively, accounted for 5.07% to 6.78%, 57.54% to 73.94%, 19.32% to 35.18%, and 0.04% to 0.10%; of the total lipids. Oleic and linoleic acid were inversely correlated (r=-0.99, P= 0.05) and together accounted for 91.16% to 94.29% of the total soluble lipids. Statistically, fattyacid composition was significantly affected by cultivar and county.

This invention relates to plant fatty acyl hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acyl hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fattyacids in transgenic plants. In addition, the use of genes encoding fattyacid hydroxylases or desaturases to alter the level of lipid fattyacid unsaturation in transgenic plants is described.

This invention relates to plant fatty acyl hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acyl hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fattyacids in transgenic plants. In addition, the use of genes encoding fattyacid hydroxylases or desaturases to alter the level of lipid fattyacid unsaturation in transgenic plants is described.

The effects of low extracellular pH and intracellular accumulation of weak organic acids were compared with respect to fattyacid synthesis by whole cells of Mycobacterium tuberculosis and Mycobacterium smegmatis. The profile of fattyacids synthesized during exposure to benzoic, nicotinic, or pyrazinoic acids, as well as that observed during intracellular hydrolysis of the corresponding amides, was not a direct consequence of modulation of fattyacid synthesis by these compounds but reflected the response to inorganic acid stress. Analysis of fattyacid synthesis in crude mycobacterial cell extracts demonstrated that pyrazinoic acid failed to directly modulate the fattyacid synthase activity catalyzed by fattyacid synthase I (FAS-I). However, fattyacid synthesis was irreversibly inhibited by 5-chloro-pyrazinamide in a time-dependent fashion. Moreover, we demonstrate that pyrazinoic acid does not inhibit purified mycobacterial FAS-I, suggesting that this enzyme is not the immediate target of pyrazinamide.

Fattyacids (n-alcanoic acids) are common compounds in numerous anthropogenic and natural emissions. According to Rogge et al. (1993), catalyst-equipped automobiles emitted more than 600 μg km-1 of fattyacids which was over 50% of all identified organics in fine aerosol emissions. Coal burning produces fattyacids ranging from about 1700 mg kg-1 for bituminous coal to over 10000 mg kg-1 for lignite (Oros and Simoneit, 2000). Similarly, biomass burning is an important source for aerosol fattyacids. They are the major identified compound group in deciduous tree smoke, their total emission factor being measured as 1589 mg kg-1 which was 56% of all identified organic compounds (Oros and Simoneit, 2001a). Large amounts of fattyacid are also emitted from burning of conifer trees and grass (Oros and Simoneit, 2001a; Simoneit, 2002). Fattyacids have been reported to be major constituents of marine aerosols in many investigations (Barger and Garrett, 1976; Gagosian et. al, 1981; Sicre et al., 1990; Stephanou, 1992). It has been suggested that as the marine aerosol particles form, they acquire a coating of organic surfactants (Blanchard, 1964; Gill et al., 1983; Middlebrook et al., 1998; Ellison et al., 1999). Amphiphilic molecules, including lipids, can be assembled as monomolecular layers at air/water interfaces as well as transported to a solid support. Recently, we could show by time-of-flight secondary ion mass spectrometry that fattyacids are important ingredients of the outermost surface layer of the sea-salt aerosol particles (Tervahattu et al., 2002). In their TOF-SIMS studies on the surface composition of atmospheric aerosols, Peterson and Tyler (2002) found fattyacids on the surface of Montana forest fire particles. In this work we have studied by TOF-SIMS the surface chemical composition of aerosol particles emitted from field fires in the Baltic and other East European countries and transported to Finland as well as aerosol particles transported from

The aim of this study was to determine the fattyacid composition and trans fattyacid and fattyacid contents of breast milk in Turkish women and to find the effect of breastfeeding mothers' diet on trans fattyacid and fattyacid composition. Mature milk samples obtained from 50 Turkish nursing women were analyzed. Total milk lipids extracts were transmethylated and analyzed by using gas liquid chromatography to determine fattyacids contents. A questionnaire was applied to observe eating habits and 3 days dietary records from mothers were obtained. Daily dietary intake of total energy and nutrients were estimated by using nutrient database. The mean total trans fattyacids contents was 2.13 +/- 1.03%. The major sources of trans fattyacids in mothers' diets were margarines-butter (37.0%), bakery products and confectionery (29.6%). Mothers who had high level of trans isomers in their milk consumed significantly higher amounts of these products. Saturated fattyacids, polyunsaturated fattyacids and monounsaturated fattyacids of human milk constituted 40.7 +/- 4.7%, 26.9 +/- 4.2% and 30.8 +/- 0.6% of the total fattyacids, respectively. The levels of fattyacids in human milk may reflect the current diet of the mother as well as the diet consumed early in pregnancy. Margarines, bakery products and confectionery are a major source of trans fattyacids in maternal diet in Turkey.

The fattyacid composition of the major lipids of the chloroplast membranes, the mono- and digalactosyl diglycerides, can be definably altered with various substituted pyridazinones. Galactolipid fattyacid composition of wheat (Triticum aestivum L.) can be altered so that there is a decrease in linolenic acid accompanied by an increase in linoleic acid without a shift in the relative proportion of saturated to unsaturated fattyacids; the fattyacid composition can be shifted toward a higher proportion of saturated fattyacids; or the fattyacid composition of the monogalactosyl diglycerides can be altered in preference to the digalactosyl diglycerides. Also, the light-mediated parallel accumulation of chlorophyll and linolenic acid can be separated with a substituted pyridazinone. The substituted pyridazinones may be useful tools in clarifying the role the galactolipids and their component fattyacids play in the structure and function of chloroplast membranes in higher plants. PMID:16659420

The functionality of the eukaryotic cell depends on the cell membrane, the genetic information and action of different organelles with or without the presence of membranes. The functionality of the cell membrane and organelles containing it depends primarily on the type and location of fattyacids in the phospholipids and the type of enzymes associated with them, this allows the fattyacids to be metabolized to new species that exert various functions. From this perspective, some essential fattyacids (EFAs) that produce metabolites that exert health benefits are identified, (for example antiinflammatory, neuroprotection, etc) and exert negative effects metabolites (eg inflammation, necrosis promoters, atheroma, etc.) are also generated. In general, these adverse or beneficial effects depend on the ratio of omega-6/omega-3 obtained in the diet. Thus, the higher this ratio is more negative effect; therefore the challenge of the current supply is obtained through food consumption, lower ratios in these fattyacids. The present review aims to present recent evidence on the effects of some AGEs, and the role of diet in maintaining health.

Fattyacid biosynthesis from (1-{sup 14}C)acetate was optimized in plastids isolated from primary root tips of 7-day-old germinating pea seeds. Fattyacid synthesis was maximum at approximately 80 nmoles/hr/mg protein in the presence of 200 {mu}M acetate, 0.5 mM each of NADH, NADPH and CoA, 6 mM each of ATP and MgCl{sub 2}, 1 mM each of the MnCl{sub 2} and glycerol-3-phosphate, 15 mM KHCO{sub 3}, and 0.1M Bis-tris-propane, pH 8.0 incubated at 35C. At the standard incubation temperature of 25C, fattyacid synthesis was linear from up to 6 hours with 80 to 100 {mu}g/mL plastid protein. ATP and CoA were absolute requirements, whereas KHCO{sub 3}, divalent cations and reduced nucleotides all improved activity by 80 to 85%. Mg{sup 2+} and NADH were the preferred cation and nucleotide, respectively. Dithiothreitol and detergents were generally inhibitory. The radioactive products of fattyacid biosynthesis were approximately 33% 16:0, 10% 18:0 and 56% 18:1 and generally did not vary with increasing concentrations of each cofactor.

The melting of alkyl chains in the saturated fattyacid zinc soaps of different chain lengths, Zn(C(n)H(2n+1)COO)(2); n = 11, 13, 15, and 17, have been investigated by powder X-ray diffraction, differential scanning calorimetry, and vibrational spectroscopy. These compounds have a layer structure with the alkyl chains arranged as tilted bilayers and with all methylene chains adopting a planar, all-trans conformation at room temperature. The saturated fattyacid zinc soaps exhibit a single reversible melting transition with the associated enthalpy change varying linearly with alkyl chain length, but surprisingly, the melting temperature remaining constant. Melting is associated with changes in the conformation of the alkyl chains and in the nature of coordination of the fattyacid to zinc. By monitoring features in the infrared spectra that are characteristic of the global conformation of the alkyl chains, a quantitative relation between conformational disorder and melting is established. It is found that, irrespective of the alkyl chain length, melting occurs when 30% of the chains in the soap are disordered. These results highlight the universal nature of the melting of saturated fattyacid zinc soaps and provide a simple explanation for the observed phenomena.

Asthma is one of the most common and prevalent problems worldwide affecting over 300 million individuals. There is some evidence from observational and intervention studies to suggest a beneficial effect of n-3 PUFA in inflammatory diseases, specifically asthma. Marine-based n-3 PUFA have therefore been proposed as a possible complementary/alternative therapy for asthma. The proposed anti-inflammatory effects of n-3 fattyacids may be linked to a change in cell membrane composition. This altered membrane composition following n-3 fattyacid supplementation (primarily EPA and DHA) can modify lipid mediator generation via the production of eicosanoids with a reduced inflammatory potential/impact. A recently identified group of lipid mediators derived from EPA including E-series resolvins are proposed to be important in the resolution of inflammation. Reduced inflammation attenuates the severity of asthma including symptoms (dyspnoea) and exerts a bronchodilatory effect. There have been no major health side effects reported with the dietary supplementation of n-3 fattyacids or their mediators; consequently supplementing with n-3 fattyacids is an attractive non-pharmacological intervention which may benefit asthma.

The role of polyunsaturated fattyacids and their metabolites for the cause and treatment of psychotic disorders are widely discussed. The efficacy as an augmenting agent in chronic schizophrenia seems to be small or not present, however epidemiological data, as well as some recent controlled studies in emerging psychosis point towards possible preventive effects of long-chain polyunsaturated fattyacids in early and very early stages of psychotic disorders and some potential secondary or tertiary beneficial long-term effects in later, more chronic stages, in particular for metabolic or extra-pyramidal side effects. In this comprehensive review, we describe the physiology and metabolism of polyunsaturated fattyacids, phospholipases, epidemiological evidence and the effect of these fattyacids on the brain and neurodevelopment. Furthermore, we examine the available evidence in indicated prevention in emerging psychosis, monotherapy, add-on therapy and tolerability. The neuroprotective potential of n-3 LC-PUFAs for indicated prevention, i.e. delaying transition to psychosis in high-risk populations needs to be further explored.

Fattyacid amino acid conjugates (FACs) have been found in noctuid as well as sphingid caterpillar oral secretions; in particular, volicitin [N-(17-hydroxylinolenoyl)-L-glutamine] and its biochemical precursor, N-linolenoyl-L-glutamine, are known elicitors of induced volatile emissions in corn plants. These induced volatiles, in turn, attract natural enemies of the caterpillars. In a previous study, we showed that N-linolenoyl-L-glutamine in larval Spodoptera litura plays an important role in nitrogen assimilation which might be an explanation for caterpillars synthesizing FACs despite an increased risk of attracting natural enemies. However, the presence of FACs in lepidopteran species outside these families of agricultural interest is not well known. We conducted FAC screening of 29 lepidopteran species, and found them in 19 of these species. Thus, FACs are commonly synthesized through a broad range of lepidopteran caterpillars. Since all FAC-containing species had N-linolenoyl-L-glutamine and/or N-linoleoyl-L-glutamine in common, and the evolutionarily earliest species among them had only these two FACs, these glutamine conjugates might be the evolutionarily older FACs. Furthermore, some species had glutamic acid conjugates, and some had hydroxylated FACs. Comparing the diversity of FACs with lepidopteran phylogeny indicates that glutamic acid conjugates can be synthesized by relatively primitive species, while hydroxylation of fattyacids is limited mostly to larger and more developed macrolepidopteran species.

Fattyacids are primary metabolites synthesized by complex, elegant, and essential biosynthetic machinery. Fattyacid synthases resemble an iterative assembly line, with an acyl carrier protein conveying the growing fattyacid to necessary enzymatic domains for modification. Each catalytic domain is a unique enzyme spanning a wide range of folds and structures. Although they harbor the same enzymatic activities, two different types of fattyacid synthase architectures are observed in nature. During recent years, strained petroleum supplies have driven interest in engineering organisms to either produce more fattyacids or specific high value products. Such efforts require a fundamental understanding of the enzymatic activities and regulation of fattyacid synthases. Despite more than one hundred years of research, we continue to learn new lessons about fattyacid synthases' many intricate structural and regulatory elements. In this review, we summarize each enzymatic domain and discuss efforts to engineer fattyacid synthases, providing some clues to important challenges and opportunities in the field.

Fattyacids are primary metabolites synthesized by complex, elegant, and essential biosynthetic machinery. Fattyacid synthases resemble an iterative assembly line, with an acyl carrier protein conveying the growing fattyacid to necessary enzymatic domains for modification. Each catalytic domain is a unique enzyme spanning a wide range of folds and structures. Although they harbor the same enzymatic activities, two different types of fattyacid synthase architectures are observed in nature. During recent years, strained petroleum supplies have driven interest in engineering organisms to either produce more fattyacids or specific high value products. Such efforts require a fundamental understanding of the enzymatic activities and regulation of fattyacid synthases. Despite more than one hundred years of research, we continue to learn new lessons about fattyacid synthases' many intricate structural and regulatory elements. Lastly, in this review, we summarize each enzymatic domain and discuss efforts to engineer fattyacid synthases, providing some clues to important challenges and opportunities in the field.

Fattyacids are primary metabolites synthesized by complex, elegant, and essential biosynthetic machinery. Fattyacid synthases resemble an iterative assembly line, with an acyl carrier protein conveying the growing fattyacid to necessary enzymatic domains for modification. Each catalytic domain is a unique enzyme spanning a wide range of folds and structures. Although they harbor the same enzymatic activities, two different types of fattyacid synthase architectures are observed in nature. During recent years, strained petroleum supplies have driven interest in engineering organisms to either produce more fattyacids or specific high value products. Such efforts require a fundamental understanding of the enzymatic activities and regulation of fattyacid synthases. Despite more than one hundred years of research, we continue to learn new lessons about fattyacid synthases’ many intricate structural and regulatory elements. In this review, we summarize each enzymatic domain and discuss efforts to engineer fattyacid synthases, providing some clues to important challenges and opportunities in the field. PMID:25360565

Ammonolysis of fattyacids to the corresponding fattyacid amides is efficiently catalysed by Candida antartica lipase (Novozym 435). In the present paper lipase-catalysed synthesis of erucamide by ammonolysis of erucic acid and urea in organic solvent medium was studied and optimal conditions for fatty amides synthesis were established. In this process erucic acid gave 88.74 % pure erucamide after 48 hour and 250 rpm at 60 degrees C with 1:4 molar ratio of erucic acid and urea, the organic solvent media is 50 ml tert-butyl alcohol (2-methyl-2-propanol). This process for synthesis is economical as we used urea in place of ammonia or other amidation reactant at atmospheric pressure. The amount of catalyst used is 3 %.

The epidemic character of depressive disorders has prompted further research into dietary habits that could make an etiological contribution. One clear change in the diet of the population in developed countries has been the replacement of omega-3 polyunsaturated fattyacids by saturated fats and trans-fats as well as by omega-6 polyunsaturated fattyacids. Omega-3 and omega-6 fattyacids are essential fattyacids, and the members of the -3 and -6 series are crucial for human health. In biochemical processes there is a competition between these two series. A higher dietary intake of omega-6 results in the excessive incorporation of these molecules in the cell membrane with numerous pathological consequences, presumably due to the formation of proinflammatory eicosanoids. Members of the omega-3 family and their derivatives modulate the inflammatory action. Essential fattyacids play a major role in brain development and brain functioning. The omega-3 series members docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) provide fluidity to the cell membrane, facilitating certain processes including neurotransmission and ion channel flow. It is thought that omega-3 deficiency during the fetal and postnatal period may have a long-term effect at various levels. Epidemiological studies have demonstrated a positive association between omega-3 deficits and mood disorders. As for treatment, there is convincing evidence that add-on omega-3 fattyacids to standard antidepressant pharmacotherapy results in improved mood. There is no evidence that fattyacid monotherapy has a mood-elevating effect, with a possible exception for childhood depression. There are indications that omega-3 has a prophylactic effect on perinatal depression and has a negative effect on natural killer cell activity and T-lymphocyte function. These observations need further study in view of the popularity of self-medication.

Inflammation, characterized by the activation of both resident and infiltrated immune cells, is accompanied by increased production of oxidizing and nitrating species. Nitrogen dioxide, the proximal nitrating species formed under these conditions, reacts with unsaturated fattyacids to yield nitroalkene derivatives. These electrophilic products modulate protein function via post-translational modification of susceptible nucleophilic amino acids. Nitroalkenes react with Keap1 to instigate Nrf2 signaling, activate heat shock response gene expression, and inhibit NF-κB-mediated signaling, inducing net anti-inflammatory and tissue-protective metabolic responses. We report the purification and characterization of a NADPH-dependent liver enzyme that reduces the nitroalkene moiety of nitro-oleic acid, yielding the inactive product nitro-stearic acid. Prostaglandin reductase-1 (PtGR-1) was identified as a nitroalkene reductase by protein purification and proteomic studies. Kinetic measurements, inhibition studies, immunological and molecular biology approaches as well as clinical analyses confirmed this identification. Overexpression of PtGR-1 in HEK293T cells promoted nitroalkene metabolism to inactive nitroalkanes, an effect that abrogated the Nrf2-dependent induction of heme oxygenase-1 expression by nitro-oleic acid. These results situate PtGR-1 as a critical modulator of both the steady state levels and signaling activities of fattyacid nitroalkenes in vivo. PMID:23878198

Seminal plasma contains various biochemical components associated with sperm function. However, there is limited information regarding the fattyacid composition of seminal plasma and their effect on sperm. The aim of this study was to identify the fattyacid content in canine seminal plasma using gas chromatography. Twelve ejaculates were studied, the seminal plasma was obtained by centrifugation and then the lipids were extracted, methylated and analysed by chromatography. The total lipids in the seminal plasma were 2.5 ± 0.3%, corresponding to 85% saturated fattyacids (SFA) and 15% unsaturated fattyacids (UFA). The greatest proportions of SFA were palmitic acid (30.4%), stearic acid (23.4%) and myristic acid (5.3%) and of UFA oleic acid (9.0%). Therefore, the protocols and techniques used enabled the identification of 18 different fattyacids in canine seminal plasma, which constitutes a good method to evaluate and quantify the fattyacid profile in this species.

The influence of fattyacids on ileal absorption of water, electrolytes, glucose, and taurocholate was examined in Thirty-Vella fistulas in five mongrel dogs. Fattyacid absorption also was measured. Segments of terminal ileum were perfused at steady state with isotonic electrolyte solutions containing 11.2 mM glucose, 4.5 mM taurocholate, and 0.1-5.0 mM fattyacid. Three C18 fattyacids, oleic acid, 10(9)-hydroxystearic acid, and ricinoleic acid, completely inhibited water absorption at 5 mM. Sodium, chloride, and potassium absorptions were inhibited in parallel with absorption of water. Differences between the potencies of C18 fattyacids were apparent when lesser concentrations were perfused. Dodecanoic and decanoic acids were as effective as C18 fattyacids at 5 mM but octanoic and hexanoic acids were ineffective. The polar group of C18 fattyacids was modified by conjugating oleic and ricinoleic acids with taurine. When these compounds and a substituted C18 fattyacid, p-n-decylbenzenesulfonate, were perfused, water absorption was also inhibited. Short-chain fattyacids (C3 and C4) and their hydroxylated derivatives were ineffective at 5 mM. When water absorption was inhibited, absorption of glucose and taurocholate was decreased. We speculate that the phenomenon of inhibition of water and electrolyte absorption by fattyacids may be relevant to steatorrhea and diarrhea in man. Images PMID:4808636

... AGENCY 40 CFR Part 180 Polyoxyalkylated Glycerol FattyAcid Esters; Tolerance Exemption AGENCY... from the requirement of a tolerance for residues of polyoxyalkylated glycerol fattyacid esters; the... unsaturated, fattyacids containing up to 15% water by weight reacted with a minimum of three moles of...

Natural occurring fattyacids are a large and complex class of compounds found in plants and animals. Fattyacids are abundant and of interest because of their renewability, biodegradability, biocompatibility, low cost, and fascinating chemistry. Of the many fattyacids, only 20-25 of them are widel...

Thespesia populnea belongs to the plant family of Malvaceae which contain cyclopropane and cyclopropene fattyacids. However, previous literature reports vary regarding the content of these compounds in Thespesia populnea seed oil. In this work, the content of malvalic acid (8,9-methylene-9-heptade...

Nonalcoholic fatty liver disease (NAFLD) is characterized by hepatic lipid accumulation which starts with simple hepatic steatosis and may progress toward inflammation (nonalcoholic steatohepatitis [NASH]). Fattyacid synthase (FASN) catalyzes the last step in fattyacid biosynthesis, and thus, it is believed to be a major determinant of the maximal hepatic capacity to generate fattyacids by de novo lipogenesis. The aim of this study was to analyze the correlation between hepatic steatosis and inflammation with FASN expression. In vitro incubation of primary human hepatocytes with fattyacids dose-dependently induced cellular lipid-accumulation and FASN expression, while stimulation with TNF did not affect FASN levels. Further, hepatic FASN expression was significantly increased in vivo in a murine model of hepatic steatosis without significant inflammation but not in a murine NASH model as compared to control mice. Also, FASN expression was not increased in mice subjected to bile duct ligation, an experimental model characterized by severe hepatocellular damage and inflammation. Furthermore, FASN expression was analyzed in 102 human control or NAFLD livers applying tissue micro array technology and immunohistochemistry, and correlated significantly with the degree of hepatic steatosis, but not with inflammation or ballooning of hepatocytes. Quantification of FASN mRNA expression in human liver samples confirmed significantly higher FASN levels in hepatic steatosis but not in NASH, and expression of SREBP1, which is the main transcriptional regulator of FASN, paralleled FASN expression levels in human and experimental NAFLD. In conclusion, the transcriptional induction of FASN expression in hepatic steatosis is impaired in NASH, while hepatic inflammation in the absence of steatosis does not affect FASN expression, suggesting that FASN may serve as a new diagnostic marker or therapeutic target for the progression of NAFLD.

Intake of marine-based n-3 fattyacids (EPA, docosapentaenoic acid and DHA) is recommended to prevent CHD. Stearidonic acid (SDA), a plant-based n-3 fattyacid, is a precursor of EPA and may be more readily converted to EPA than a-linolenic acid (ALA). While transgenic soyabeans might supply SDA at ...

In this work, the fattyacid profiles of the seed oils of Albizia lebbeck and Albizia saman (Samanea saman) are reported. The oils were analyzed by GC, GC-MS, and NMR. The most prominent fattyacid in both oils is linoleic acid (30-40%), followed by palmitic acid and oleic acid for A. lebbeck and ol...

The objective of the present study was to assess the effect of elevating epoxygenated fattyacids on retinal vascular inflammation. To stimulate inflammation we utilized TNFα, a potent pro-inflammatory mediator that is elevated in the serum and vitreous of diabetic patients. In TNFα-stimulated primary human retinal microvascular endothelial cells, total levels of epoxyeicosatrienoic acids (EETs), but not epoxydocosapentaenoic acids (EDPs), were significantly decreased. Exogenous addition of 11,12-EET or 19,20-EDP when combined with 12-(3-adamantane-1-yl-ureido)-dodecanoic acid (AUDA), an inhibitor of epoxide hydrolysis, inhibited VCAM-1 and ICAM-1 expression and protein levels; conversely the diol product of 19,20-EDP hydrolysis, 19,20-DHDP, induced VCAM1 and ICAM1 expression. 11,12-EET and 19,20-EDP also inhibited leukocyte adherence to human retinal microvascular endothelial cell monolayers and leukostasis in an acute mouse model of retinal inflammation. Our results indicate that this inhibition may be mediated through an indirect effect on NFκB activation. This is the first study demonstrating a direct comparison of EET and EDP on vascular inflammatory endpoints, and we have confirmed a comparable efficacy from each isomer, suggesting a similar mechanism of action. Taken together, these data establish that epoxygenated fattyacid elevation will inhibit early pathology related to TNFα-induced inflammation in retinal vascular diseases. PMID:27966642

In this study, the physiological effects of fattyacids with conjugated double bonds were widely examined in vitro and in vivo. Initially, a method for determination of conjugated fattyacids in food and biological samples was established. I then clarified that the oxidative stability of conjugated fattyacids was improved by the form of triacylglycerol and addition of an antioxidant, and the influence of this effect on the metabolism and pharmacokinetics of conjugated fattyacids was clarified in vivo. In addition, antitumor, anti-angiogenesis, and antiobesity effects of conjugated fattyacids were found for the first time, thus demonstrating the usefulness of conjugated fattyacids. This communication mainly outlines the data obtained for conjugated linolenic acid. In addition, this review summarizes my research on conjugated fattyacid.

According to report, temperature of growth of thermotolerant, methane-oxidizing bacterium Methylococcus capsulatus (Bath) affects both proportion of monounsaturated fattyacids and cis/trans ratio of these acids in cell membrane. Because suboptimum growth temperature is potential stress factor, it may be possible to use such cis/trans ratios as indices of stresses upon methane-oxidizing microbial communities. Research in microbiology of methanotrophs increasing because of possible commercial exploitation of these organisms as biocatalysts or as sources of useful polymers; knowledge of effect of temperature on ability of methanotrophs to utilize methane useful in optimization of conditions of growth.

cis-Cyclopropane fattyacids (cis-CFAs) are widespread constituents of the seed oils of subtropical plants, membrane components of bacteria and protozoa, and the fats and phospholipids of animals. We describe a systematic approach to the synthesis of enantiomeric pairs of four cis-CFAs: cis-9,10-methylenehexadecanoic acid, lactobacillic acid, dihydromalvalic acid, and dihydrosterculic acid. The approach commences with Rh2(OAc)4-catalyzed cyclopropenation of 1-octyne and 1-decyne, and hinges on the preparative scale chromatographic resolution of racemic 2-alkylcycloprop-2-ene-1-carboxylic acids using a homochiral Evan's auxiliary. Saturation of the individual diastereomeric N-cycloprop-2-ene-1-carbonylacyloxazolidines, followed by elaboration to alkylcyclopropylmethylsulfones, allowed Julia-Kocienski olefination with various ω-aldehyde-esters. Finally, saponification and diimide reduction afforded the individual cis-CFA enantiomers.

Short-chain fattyacids (SCFAs), such as butyric acid, have a broad range of applications in chemical and fuel industries. Worldwide demand of sustainable fuels and chemicals has encouraged researchers for microbial synthesis of SCFAs. In this study we compared three thioesterases, i.e., TesAT from Anaerococcus tetradius, TesBF from Bryantella formatexigens and TesBT from Bacteroides thetaiotaomicron, for production of SCFAs in Escherichia coli utilizing native fattyacid synthesis (FASII) pathway and modulated the genetic and bioprocess parameters to improve its yield and productivity. E. coli strain expressing tesBT gene yielded maximum butyric acid titer at 1.46 g L-1, followed by tesBF at 0.85 g L-1 and tesAT at 0.12 g L-1. The titer of butyric acid varied significantly depending upon the plasmid copy number and strain genotype. The modulation of genetic factors that are known to influence long chain fattyacid production, such as deletion of the fadD and fadE that initiates the fattyacid degradation cycle and overexpression of fadR that is a global transcriptional activator of fattyacid biosynthesis and repressor of degradation cycle, did not improve the butyric acid titer significantly. Use of chemical inhibitor cerulenin, which restricts the fattyacid elongation cycle, increased the butyric acid titer by 1.7-fold in case of TesBF, while it had adverse impact in case of TesBT. In vitro enzyme assay indicated that cerulenin also inhibited short chain specific thioesterase, though inhibitory concentration varied according to the type of thioesterase used. Further process optimization followed by fed-batch cultivation under phosphorous limited condition led to production of 14.3 g L-1 butyric acid and 17.5 g L-1 total free fattyacid at 28% of theoretical yield. This study expands our understanding of SCFAs production in E. coli through FASII pathway and highlights role of genetic and process optimization to enhance the desired product. PMID:27466817

The continued increase in human population has resulted in the rise in the demand as well as the price of edible oils, leading to the search for alternative unconventional sources of oils, particularly in the developing countries. There are hundreds of un- or underexplored plant seeds rich in oil suitable for edible or industrial purposes. Many of them are rich in polyunsaturated essential fattyacids, which establish their utility as "healthy oils." Some agrowaste products such as rice bran have gained importance as a potential source of edible oil. Genetic modification has paved the way for increasing the oil yields and improving the fattyacid profiles of traditional as well as unconventional oilseeds. Single cell oils are also novel sources of edible oil. Some of these unconventional oils may have excellent potential for medicinal and therapeutic uses, even if their low oil contents do not promote commercial production as edible oils.

Two cell lines of normal (CRL 1475, GM5565) and of familial hypercholesterolemia (FH) (CM 486,488) fibroblasts were preincubated with medium containing the growth factor ITS, 2.5 mg/ml fattyacid-free BSA, or 35.2 ..mu..mol/ml of these fattyacids complexed with 2.5 mg BSA/ml: stearic (18:0), caprylic (8:0), oleic (18:1;9), linoleic (18:2;9,12), linolenic (18:3;9,12,15), docosahexaenoic (22:6;4,7,10,13,16,19)(DHA) or eicosapentaenoic (20:5;5,8,11,14,17)(EPA). After 20 h, cells were incubated for 2 h with 0.2 ..mu..Ci (/sup 14/C)acetate/ml. Cells were hydrolyzed; an aliquot was quantitated for radioactivity and protein. After saponification and extraction with hexane, radioactivity in the aqueous and organic phases was determined. The FH cells always incorporated 30-90% more acetate/mg protein than normal cells but the pattern of the fattyacid effects was similar in both types. When the values were normalized to 1 for the BSA-only group, cells with ITS had the greatest (/sup 14/C)acetate incorporation (1.45) followed by the caprylic group (1.14). Cells incubated with 18:3, 20:6 or 22:6 incorporated about the same amount as BSA-only. Those preincubated with 18:2, 18:1, 18:0 showed the least acetate incorporation (0.87, 0.59 and 0.52, respectively). The percentage of total /sup 14/C counts which extracted into hexane was much greater in FH cells; however, these values varied with the fattyacid, e.g., 1.31(18:0) and 0.84(8:0) relative to 1(BSA).

A common feature of ageing is the alteration in tissue distribution and composition, with a shift in fat away from lower body and subcutaneous depots to visceral and ectopic sites. Redistribution of adipose tissue towards an ectopic site can have dramatic effects on metabolic function. In skeletal muscle, increased ectopic adiposity is linked to insulin resistance through lipid mediators such as ceramide or DAG, inhibiting the insulin receptor signalling pathway. Additionally, the risk of developing cardiovascular disease is increased with elevated visceral adipose distribution. In ageing, adipose tissue becomes dysfunctional, with the pathway of differentiation of preadipocytes to mature adipocytes becoming impaired; this results in dysfunctional adipocytes less able to store fat and subsequent fat redistribution to ectopic sites. Low grade systemic inflammation is commonly observed in ageing, and may drive the adipose tissue dysfunction, as proinflammatory cytokines are capable of inhibiting adipocyte differentiation. Beyond increased ectopic adiposity, the effect of impaired adipose tissue function is an elevation in systemic free fattyacids (FFA), a common feature of many metabolic disorders. Saturated fattyacids can be regarded as the most detrimental of FFA, being capable of inducing insulin resistance and inflammation through lipid mediators such as ceramide, which can increase risk of developing atherosclerosis. Elevated FFA, in particular saturated fattyacids, maybe a driving factor for both the increased insulin resistance, cardiovascular disease risk and inflammation in older adults.

Fattyacids are the preferred oxidative substrates of the heart, skeletal muscles, kidney cortex and liver in adult mammals. They are supplied to these tissues either as nonesterified fattyacids (NEFA), or as triglycerides after hydrolysis by lipoprotein lipase. During fetal life, tissue capacity to oxidize NEFA is very low, even in species in which the placental transfer of NEFA and carnitine is high. At birth, the ability to oxidize NEFA from endogenous sources or from milk (a high-fat diet) develops rapidly in various tissues and remains very high throughout the suckling period. Ketogenesis appears in the liver by 6 to 12 hrs after birth, and the ketone bodies are used as oxidative fuels by various tissues during the suckling period. At the time of weaning, the transition from a high-fat to a high-carbohydrate diet is attended by a progressive decrease in the ketogenic capacity of the liver, whereas other tissues (skeletal muscle, heart, kidney) maintain a high capacity for NEFA oxidation. The nutritional and hormonal factors involved in changes in fattyacid oxidation during development are discussed.

With the increasing concern for health and nutrition, dietary fat has attracted considerable attention. The composition of fattyacids in a diet is important since they are associated with major diseases, such as cancers, diabetes, and cardiovascular disease. The biosynthesis of unsaturated fattyacids (UFA) requires the expression of dietary fat-associated genes, such as SCD, FADS1, FADS2, and FADS3, which encode a variety of desaturases, to catalyze the addition of a double bond in a fattyacid chain. Recent studies using new molecular techniques and genomics, as well as clinical trials have shown that these genes and UFA are closely related to physiological conditions and chronic diseases; it was found that the existence of alternative transcripts of the desaturase genes and desaturase isoforms might affect human health and lipid metabolism in different ways. In this review, we provide an overview of UFA and desaturases associated with human health and nutrition. Moreover, recent findings of UFA, desaturases, and their associated genes in human systems are discussed. Consequently, this review may help elucidate the complicated physiology of UFA in human health and diseases.

The novel fattyacid 7-methyl-8-hexadecenoic (1) was identified in the marine spongeDesmapsama anchorata. Other interesting fattyacids identified were 14-methyl-8-hexadecenoic (2), better known through its methyl ester as one of the components of the sex attractant of the female dermestid beetle, and the saturated fattyacid 3-methylheptadecanoic (3), known to possess larvicidal activity. The main phospholipid fattyacids encountered inD. anchorata were palmitic (16∶0), behenic (22∶0) and 5,9-hexacosadienoic acid (26∶2), which together accounted for 50% of the total phospholipid fattyacid mixture.

These studies defined the expression patterns of genes involved in fattyacid transport, activation and trafficking using quantitative PCR (qPCR) and established the kinetic constants of fattyacid transport in an effort to define whether vectorial acylation represents a common mechanism in different cell types (3T3-L1 fibroblasts and adipocytes, Caco-2 and HepG2 cells and three endothelial cell lines (b-END3, HAEC, and HMEC)). As expected, fattyacid transport protein (FATP)1 and long-chain acyl CoA synthetase (Acsl)1 were the predominant isoforms expressed in adipocytes consistent with their roles in the transport and activation of exogenous fattyacids destined for storage in the form of triglycerides. In cells involved in fattyacid processing including Caco-2 (intestinal-like) and HepG2 (liver-like), FATP2 was the predominant isoform. The patterns of Acsl expression were distinct between these two cell types with Acsl3 and Acsl5 being predominant in Caco-2 cells and Acsl4 in HepG2 cells. In the endothelial lines, FATP1 and FATP4 were the most highly expressed isoforms; the expression patterns for the different Acsl isoforms were highly variable between the different endothelial cell lines. The transport of the fluorescent long-chain fattyacid C(1)-BODIPY-C(12) in 3T3-L1 fibroblasts and 3T3-L1 adipocytes followed typical Michaelis-Menten kinetics; the apparent efficiency (k(cat)/K(T)) of this process increases over 2-fold (2.1 x 10(6)-4.5 x 10(6)s(-1)M(-1)) upon adipocyte differentiation. The V(max) values for fattyacid transport in Caco-2 and HepG2 cells were essentially the same, yet the efficiency was 55% higher in Caco-2 cells (2.3 x 10(6)s(-1)M(-1) versus 1.5 x 10(6)s(-1)M(-1)). The kinetic parameters for fattyacid transport in three endothelial cell types demonstrated they were the least efficient cell types for this process giving V(max) values that were nearly 4-fold lower than those defined form 3T3-L1 adipocytes, Caco-2 cells and HepG2 cells. The

The central nervous system is highly enriched in long-chain polyunsaturated fattyacid (PUFA) of the omega-6 and omega-3 series. The presence of these fattyacids as structural components of neuronal membranes influences cellular function both directly, through effects on membrane properties, and also by acting as a precursor pool for lipid-derived messengers. An adequate intake of omega-3 PUFA is essential for optimal visual function and neural development. Furthermore, there is increasing evidence that increased intake of the long-chain omega-3 PUFA, eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), may confer benefits in a variety of psychiatric and neurological disorders, and in particular neurodegenerative conditions. However, the mechanisms underlying these beneficial effects are still poorly understood. Recent evidence also indicates that in addition to the positive effects seen in chronic neurodegenerative conditions, omega-3 PUFA may also have significant neuroprotective potential in acute neurological injury. Thus, these compounds offer an intriguing prospect as potentially new therapeutic approaches in both chronic and acute conditions. The purpose of this article is to review the current evidence of the neurological benefits of omega-3 PUFA, looking specifically at neurodegenerative conditions and acute neurological injury.

Supplements have reached a prominent role in improving the supply of long-chain omega-3 fattyacids, such as Eicosapentaenoic acid (EPA 20:5n-3) and Docosahexaenoic acid (DHA 22:6n-3). Similar to other nutrients, the availability of omega-3 fattyacids is highly variable and determined by numerous factors. However, the question of omega-3 fattyacids bioavailability has long been disregarded, which may have contributed to the neutral or negative results concerning their effects in several studies. This review provides an overview of the influence of chemical binding form (free fattyacids bound in ethylesters, triacylglycerides or phospholipids), matrix effects (capsule ingestion with concomitant intake of food, fat content in food) or galenic form (i.e. microencapsulation, emulsification) on the bioavailability of omega-3 fattyacids. There is a need to systematically investigate the bioavailability of omega-3 fattyacids formulations, which might be a key to designing more effective studies in the future.

The determination of fattyacids and organic acids in Chinese medicinal plant Ranunculus ternatus Thunb using GC-MS was studied. The Ranunculus ternatus Thunb from Henan province was cut into less than 20 mesh pieces, then extracted by petroleum ether or ether in refluxing and esteried, and finally was determined using GC-MS. The results show that there are 23 kinds of organic compounds in the Chinese medicinal plant Ranunculus ternatus Thunb from Henan, among which 15 kinds of fattyacids were identified, including myristic acid, palmitic acid, stearic acid, oleic acid, linolenic acid, eicosanoic acid, docosanoic acid etc. The unsaturated fattyacids and oleic acid account for 58.19% and 35.68% of the total organic compounds respectively. The kinds of fattyacid in petroleum ether extract and ether extract are the same.

The chemoenzymatic synthesis of new surfactants is reported; they were prepared from unprotected carbohydrates, amino acids, and fattyacids. This study pointed out the factors that govern the possibility to enzymatically bind the carbohydrate to the amino acid.

Fattyacids (FAs) are considered strategically important platform compounds that can be accessed by sustainable microbial approaches. Here we report the reprogramming of chain-length control of Saccharomyces cerevisiae fattyacid synthase (FAS). Aiming for short-chain FAs (SCFAs) producing baker's yeast, we perform a highly rational and minimally invasive protein engineering approach that leaves the molecular mechanisms of FASs unchanged. Finally, we identify five mutations that can turn baker's yeast into a SCFA producing system. Without any further pathway engineering, we achieve yields in extracellular concentrations of SCFAs, mainly hexanoic acid (C6-FA) and octanoic acid (C8-FA), of 464 mg l−1 in total. Furthermore, we succeed in the specific production of C6- or C8-FA in extracellular concentrations of 72 and 245 mg l−1, respectively. The presented technology is applicable far beyond baker's yeast, and can be plugged into essentially all currently available FA overproducing microorganisms. PMID:28281527

The effect of all-trans retinoic acid on the proliferation of essential fattyacid (EFA)-deficient and of EFA-supplemented adult human keratinocytes was investigated. EFA-deficient cell strains were supplied with one of four different fattyacid-supplemented media at the P0 to P1 passage. All-trans retinoic acid at 0.5 or 1.0 microM was added to the cultures at the P1 to P2 passage. At passage P3, and 3 and 7 d thereafter, the cell growth rate was determined. The fattyacid content of cultures grown in each medium was measured using gas chromatography. All the EFA media "normalized" the cellular fattyacid composition and drastically decreased the cell number and total DNA and protein of the cultures. All-trans retinoic acid at 1 microM prevented the loss of cell viability and growth usually associated with EFA supplementation but did not affect the control (EFA deficient) or 18:1 fattyacid-supplemented cultures. All-trans retinoic acid at 1 microM altered the fattyacid content of the EFA-supplemented cultures. A statistically significant increase in 14:0, 14:1, 16:1, 18:1, and 20:4 fattyacids occurred, whereas the amounts of 18:0 and 18:2 fattyacids decreased. The largest changes were in 16:1 fattyacid (8-14%) and 18:2 fattyacid (12-5%). All-trans retinoic acid at 0.5 microM also affected both cell growth and fattyacid composition without induction of the CRABP II message. These studies demonstrate that all-trans retinoic acid stimulates the growth of EFA-supplemented keratinocyte cultures while also altering the fattyacid composition of the cells.

The fattyacid profiles of six seed oils of the Fabaceae (Leguminosae) family are reported and discussed. These are the seed oils of Centrosema pubescens, Clitoria ternatea, Crotalaria mucronata, Macroptilium lathyroides, Pachyrhizus erosus, and Senna alata. The most common fattyacid in the fatty a...

This invention relates to plant fatty acyl hydroxylases. Methods to use conserved amino acid or nucleotide sequences to obtain plant fatty acyl hydroxylases are described. Also described is the use of cDNA clones encoding a plant hydroxylase to produce a family of hydroxylated fattyacids in transgenic plants.

Strains of Actinobacillus actinomycetemcomitans isolated from deep pockets of patients with juvenile periodontitis were analyzed for their content of cellular fattyacids. Oral Haemophilus strains, morphologically and biochemically similar to Haemophilus aphrophilus, were also examined for their content of cellular fattyacids. The extractable lipids of the actinobacilli represented approximately 10% of the cell dry weight, with the bound lipids representing 2 to 5%. The major fattyacids consisted of myristic (C14:0) and palmitic (C16:0) acids and a C16:1 acid, possibly palmitoleic acid, accounting for 21, 35, and 31% of the total extractable fattyacids, respectively. Haemophilus strains had a similar cellular fattyacid content. PMID:7430333

Background Patients with phenylketonuria (PKU) have to follow a lifelong phenylalanine restricted diet. This type of diet markedly reduces the intake of saturated and unsaturated fattyacids especially long chain polyunsaturated fattyacids (LC-PUFA). Long-chain saturated fattyacids are substrates of mitochondrial fattyacid oxidation for acetyl-CoA production. LC-PUFA are discussed to affect inflammatory and haemostaseological processes in health and disease. The influence of the long term PKU diet on fattyacid metabolism with a special focus on platelet eicosanoid metabolism has been investigated in the study presented here. Methodology/Principal Findings 12 children with PKU under good metabolic control and 8 healthy controls were included. Activated fattyacids (acylcarnitines C6–C18) in dried blood and the cholesterol metabolism in serum were analyzed by liquid chromatographic tandem mass spectrometry (LC-MS/MS). Fattyacid composition of plasma glycerophospholipids was determined by gas chromatography. LC-PUFA metabolites were analyzed in supernatants by LC-MS/MS before and after platelet activation and aggregation using a standardized protocol. Patients with PKU had significantly lower free carnitine and lower activated fattyacids in dried blood compared to controls. Phytosterols as marker of cholesterol (re-) absorption were not influenced by the dietary fattyacid restriction. Fattyacid composition in glycerophospholipids was comparable to that of healthy controls. However, patients with PKU showed significantly increased concentrations of y-linolenic acid (C18:3n-6) a precursor of arachidonic acid. In the PKU patients significantly higher platelet counts were observed. After activation with collagen platelet aggregation and thromboxane B2 and thromboxane B3 release did not differ from that of healthy controls. Conclusion/Significance Long-term dietary fattyacid restriction influenced the intermediates of mitochondrial beta-oxidation. No functional

More than ever, new technology is having an impact on the tools of clinical microbiologists. The analysis of cellular fattyacids by gas-liquid chromatography (GLC) has become markedly more practical with the advent of the fused-silica capillary column, computer-controlled chromatography and data analysis, simplified sample preparation, and a commercially available GLC system dedicated to microbiological applications. Experience with applications in diagnostic microbiology ranges from substantial success in work with mycobacteria, legionellae, and nonfermentative gram-negative bacilli to minimal involvement with fungi and other nonbacterial agents. GLC is a good alternative to other means for the identification of mycobacteria or legionellae because it is rapid, specific, and independent of other specialized testing, e.g., DNA hybridization. Nonfermenters show features in their cellular fattyacid content that are useful in identifying species and, in some cases, subspecies. Less frequently encountered nonfermenters, including those belonging to unclassified groups, can ideally be characterized by GLC. Information is just beginning to materialize on the usefulness of cellular fattyacids for the identification of gram-positive bacteria and anaerobes, despite the traditional role of GLC in detecting metabolic products as an aid to identification of anaerobes. When species identification of coagulase-negative staphylococci is called for, GLC may offer an alternative to biochemical testing. Methods for direct analysis of clinical material have been developed, but in practical and economic terms they are not yet ready for use in the clinical laboratory. Direct analysis holds promise for detecting markers of infection due to an uncultivable agent or in clinical specimens that presently require cultures and prolonged incubation to yield an etiologic agent. PMID:1747860

We hypothesized that insulin alters plasma free fattyacid (FFA) trafficking into intramyocellular (im) long-chain acylcarnitines (imLCAC) and triglycerides (imTG). Overnight-fasted adults (n = 41) received intravenous infusions of [U-13C]palmitate (0400–0900 h) and [U-13C]oleate (0800–1400 h) to label imTG and imLCAC. A euglycemic-hyperinsulinemic (1.0 mU·kg fat-free mass−1·min−1) clamp (0800–1400 h) and two muscle biopsies (0900 h, 1400 h) were performed. The patterns of [U-13C]palmitate incorporation into imTG-palmitate and palmitoylcarnitine were similar to those we reported in overnight postabsorptive adults (saline control); the intramyocellular palmitoylcarnitine enrichment was not different from and correlated with imTG-palmitate enrichment for both the morning (r = 0.38, P = 0.02) and afternoon (r = 0.44, P = 0.006) biopsy samples. Plasma FFA concentrations, flux, and the incorporation of plasma oleate into imTG-oleate during hyperinsulinemia were ∼1/10th of that observed in the previous saline control studies (P < 0.001). At the time of the second biopsy, the enrichment in oleoylcarnitine was <25% of that in imTG-oleate and was not correlated with imTG-oleate enrichment. The intramyocellular nonesterified fattyacid-palmitate-to-imTG-palmitate enrichment ratio was greater (P < 0.05) in women than men, suggesting that sex differences in intramyocellular palmitate trafficking may occur under hyperinsulinemic conditions. We conclude that plasma FFA trafficking into imTG during hyperinsulinemia is markedly suppressed, and these newly incorporated FFA fattyacids do not readily enter the LCAC preoxidative pools. Hyperinsulinemia does not seem to inhibit the entry of fattyacids from imTG pools that were labeled under fasting conditions, possibly reflecting the presence of two distinct imTG pools that are differentially regulated by insulin. PMID:23820622

The fattyacid alcohol ester-synthesizing activity of lipoprotein lipase (LPL) was characterized using bovine milk LPL. Synthesizing activities were determined in an aqueous medium using oleic acid or trioleylglycerol as the acyl donor and equimolar amounts of long-chain alcohols as the acyl acceptor. When oleic acid and hexadecanol emulsified with gum arabic were incubated with LPL, palmityl oleate was synthesized, in a time- and dose-dependent manner. Apo-very low density lipoprotein (apoVLDL) stimulated LPL-catalyzed palmityl oleate synthesis. The apparent equilibrium ratio of fattyacid alcohol ester/oleic acid was estimated using a high concentration of LPL and a long (20 h) incubation period. The equilibrium ratio was affected by the incubation pH and the alcohol chain length. When the incubation pH was below pH 7.0 and long chain fatty acyl alcohols were used as substrates, the fattyacid alcohol ester/free fattyacid equilibrium ratio favored ester formation, with an apparent equilibrium ratio of fattyacid alcohol ester/fattyacid of about 0.9/0.1. The equilibrium ratio decreased sharply at alkaline pH (above pH 8.0). The ratio also decreased when fatty alcohols with acyl chains shorter than dodecanol were used. When a trioleoylglycerol/fatty acyl alcohol emulsion was incubated with LPL, fattyacid alcohol esters were synthesized in a dose- and time-dependent fashion. Fattyacid alcohol esters were easily synthesized from trioleoylglycerol when fatty alcohols with acyl chains longer than dodecanol were used, but synthesis was decreased with fatty alcohols with acyl chain lengths shorter than decanol, and little synthesizing activity was detected with shorter-chain fatty alcohols such as butanol or ethanol.

The fattyacid profiles of lipids from microalgae are unique. Polyunsaturated fattyacids are generally enriched in polar lipids, whereas saturated and monounsaturated fattyacids constitute the majority of fattyacids in triacylglycerols (TAG). Each species has characteristic fattyacids, and their content is positively or negatively correlated with TAGs. The marine oleaginous diatom Phaeodactylum tricornutum was used as the paradigm to determine the quantitative relationship between TAG and characteristic fattyacid content. Fattyacid profiles and TAG content of Phaeodactylum tricornutum were determined in a time course. C16:0/C16:1 and eicosapentaenoic acid (EPA, C20:5n3) were identified as characteristic fattyacids in TAGs and polar lipids, respectively. The percentage of those characteristic fattyacids in total fattyacids had a significant linear relationship with TAG content, and thus, the correlation coefficient presenting r2 were 0.96, 0.94, and 0.97, respectively. The fattyacid-based method for TAG quantification could also be applied to other microalgae such as Nannochloropsis oceanica in which the r2 of C16:0 and EPA were 0.94 and 0.97, respectively, and in Chlorella pyrenoidosa r2-values for C18:1 and C18:3 with TAG content were 0.91 and 0.99, repectively. This characteristic fattyacid-based method provided a distinct way to quantify TAGs in microalgae, by which TAGs could be measured precisely by immediate transesterification from wet biomass rather than using conventional methods. This procedure simplified the operation and required smaller samples than conventional methods. PMID:26941747

Inflammation is overall a protective response, whose main goal is to liberate the human being of cellular lesions caused by micro-organisms, toxins, allergens, etc., as well as its consequences, and of death cells and necrotic tissues. Chronic inflammation, which is detrimental to tissues, is the basic pathogenic mechanism of hypersensitivity reactions against xenobiotics. Other frequent pathologies, for instance atherosclerosis, chronic hepatitis, inflammatory bowel disease (IBD), liver cirrhosis, lung fibrosis, psoriasis, and rheumatoid arthritis are also chronic inflammatory diseases. Chemical mediators of inflammation are derived from blood plasma or different cell-type activity. Biogenic amines, eicosanoids and cytokines are within the most important mediators of inflammatory processes. The different activities of eicosanoids derived from arachidonic acid (20:4 n-6) versus those derived from eicosapentaenoic acid (20:5 n-3) are one of the most important mechanisms to explain why n-3, or omega-3, polyunsaturated fattyacids (PUFA) exhibit anti-inflammatory properties in many inflammatory diseases. Dietary supplements ranging 1-8 g per day of n-3 PUFA have been reportedly beneficial in the treatment of IBD, eczema, psoriasis and rheumatoid arthritis. In addition, recent experimental studies in rats with experimental ulcerative colitis, induced by intrarectal injection of trinitrobenzene sulphonic acid, have documented that treatment with n-3 long-chain PUFA reduces mucosal damage as assessed by biochemical and histological markers of inflammation. Moreover, the defence antioxidant system in this model is enhanced in treated animals, provided that the n-3 PUFA supply is adequately preserved from oxidation.

A silver ion HPLC procedure is described that is suitable to determine the fattyacid composition of plant seed oils. After conversion of fattyacids to p-methoxyphenacyl derivatives, it was possible to achieve baseline resolution of all fattyacid components with 0 to 3 double bonds, including the positionally isomeric 18:1 fattyacids oleic acid (cis 9-18:1), petroselinic acid (cis 6-18:1), and cis-vaccenic acid (cis 11-18:1), in aniseed oil (Pimpinella anisum, Apiaceae) by a single gradient run on a single cation exchange column laboratory converted to the silver ion form. The UV detector response (280 nm) was linearly related to the fattyacid concentration in the range 0.01 to 3.5 mg/mL.

Previous reports showed altered fattyacid content in subjects with altered sperm parameters compared to normozoospermic individuals. However, these studies focused on a limited number of fattyacids, included a short number of subjects and results varied widely. We conducted a case-control study involving 155 patients allocated into four groups, including normozoospermia (n = 33), oligoasthenoteratozoospermia (n = 32), asthenozoospermia (n = 25), and varicocoele (n = 44). Fattyacid profiling, including 30 species, was analyzed by a validated gas chromatography (GC) method on the whole seminal fluid sample. Multinomial logistic regression modeling was used to identify the associations between fattyacids and the four groups. Specimens from 15 normozoospermic subjects were also analyzed for fattyacids content in the seminal plasma and spermatozoa to study the distribution in the two compartments. Fattyacids lipidome varied markedly between the four groups. Multinomial logistic regression modeling revealed that high levels of palmitic acid, behenic acid, oleic acid, and docosahexaenoic acid (DHA) confer a low risk to stay out of the normozoospermic group. In the whole population, seminal fluid stearic acid was negatively correlated (r = -0.53), and DHA was positively correlated (r = 0.65) with sperm motility. Some fattyacids were preferentially accumulated in spermatozoa and the highest difference was observed for DHA, which was 6.2 times higher in spermatozoa than in seminal plasma. The results of this study highlight complete fattyacids profile in patients with different semen parameters. Given the easy-to-follow and rapid method of analysis, fattyacid profiling by GC method can be used for therapeutic purposes and to measure compliance in infertility trials using fattyacids supplements.

Using a technique in which substrate fattyacids are incorporated into microsomal membranes followd by comparison of their rates of desaturation or elongation with those of exogenous added fattyacids it has been found that the desaturation rate is more rapid for the membrane-bound substrate than for the added fattyacid. Moreover, the product of the membrane-bound substrate is incorporated into membrane phospholipid whereas the product of the exogenous substrate is found in di- and triacyl glycerols and in free fattyacids as well. These and other findings point to a normal sequence of reaction of membrane liqids with membrane-bound substrates involving transfer of fattyacid from phospholipid to the coupled enzyme systems without ready equilibration with the free fattyacid pool.

Emerging evidence indicates that the fattyacid composition of obesogenic diets impacts physiologic outcomes. Much attention is focused on the biologic effects of consuming monounsaturated fattyacids (MUFA) vs saturated fattyacids (SFA). We investigated the extent to which an obesogenic diet high ...

Polyunsaturated fattyacids (PUFA) of the (n-6) and (n-3) families inhibit the rate of gene transcription for a number of hepatic lipogenic and glycolytic genes, e.g., fattyacid synthase (FAS). In contrast, saturated and monounsaturated fattyacids have no inhibitory capability. The suppression of gene transcription resulting from the addition of PUFA to a high carbohydrate diet: occurs quickly (< 3 h) after its addition to a high glucose diet; can be recreated with hepatocytes cultured in a serum-free medium containing insulin and glucocorticoids; can be demonstrated in diabetic rats fed fructose; and is independent of glucagon. While the nature of the intracellular PUFA inhibitor is unclear, it appears that delta-6 desaturation is a required step in the process. Recently, the fattyacid activated nuclear factor, peroxisome-proliferator activated receptor (PPAR) was suggested to be the PUFA-response factor. However, the potent PPAR activators ETYA and Wy-14643 did not suppress hepatic expression of FAS, but did induce the PPAR-responsive gene, acyl-CoA oxidase (AOX). Similarly, treating rat hepatocytes with 20:4 (n-6) suppressed FAS expression but had no effect on AOX. Thus, it appears that the PUFA regulation of gene transcription involves a PUFA-response factor that is independent from PPAR.

Saturated fattyacids and their salts widely exist in the nature, and they are well known as important chemical materials. Their infrared spectra have been studied in detail. Nevertheless, few works on the Raman spectra characteristics of saturated fattyacids and their salts have been published before. Man-made crystals of acetic acid, stearic acid, calcium acetate, magnesium acetate, calcium stearate and magnesium stearate were investigated by means of Fourier transform Raman spectrometry for purpose of realizing their Raman spectra. Positive ions can cause the distinctions between the spectra of saturated fattyacids and their salts. The differences in mass and configuration between Ca2+ and Mg2+ result in the Raman spectra's diversity between calcium and magnesium salts of saturated fattyacids. Meanwhile, it is considered that the long carbon chain weakened the influence of different positive ions on the salts of saturated fattyacids.

New mutants of Neurospora crassa having the ufa phenotype have been isolated. Two of these mutants, like previously identified ufa mutants, require an unsaturated fattyacid for growth and are almost completely blocked in the de novo synthesis of unsaturated fattyacids. The new mutations map to a different chromosomal location than previously characterized ufa mutations. This implies that at least one additional genetic locus controls the synthesis of unsaturated fattyacids in Neurospora.

The use of microalgae for biofuel production will be beneficial to society if we can produce biofuels at large scales with minimal mechanical energy input in the production process. Understanding micro-algal physiological responses under variable environmental conditions in bioreactors is essential for the optimization of biofuel production. We demonstrate that measuring micro-algal swimming speed provides information on culture health and total fattyacid accumulation. Three strains of Chlamydomonas reinhardtii were grown heterotrophically on acetate and subjected to various levels of nitrogen starvation. Other nutrient levels were explored to determine their effect on micro-algal kinetics. Swimming velocities were measured with two-dimensional micro-particle tracking velocimetry. The results show an inverse linear relationship between normalized total fattyacid mass versus swimming speed of micro-algal cells. Analysis of RNA sequencing data confirms these results by demonstrating that the biological processes of cell motion and the generation of energy precursors are significantly down-regulated. Experiments demonstrate that changes in nutrient concentration in the surrounding media also affect swimming speed. The findings have the potential for the in situ and indirect assessment of lipid content by measuring micro-algal swimming kinetics.

The consumption of dietary fats have been long associated to chronic diseases such as obesity, diabetes, cancer, arthritis, asthma, and cardiovascular disease; although some controversy still exists in the role of dietary fats in human health, certain fats have demonstrated their positive effect in the modulation of abnormal fattyacid and eicosanoid metabolism, both of them associated to chronic diseases. Among the different fats, some fattyacids can be used as functional ingredients such as alpha-linolenic acid (ALA), arachidonic acid (AA), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), gamma-linolenic acid (GLA), stearidonic acid (STA) and conjugated linoleic acid (CLA), among others. The present review is focused on recent developments in FAs analysis, covering sample preparation methods such as extraction, fractionation and derivatization as well as new advances in chromatographic methods such as GC and HPLC. Special attention is paid to trans fattyacids due its increasing interest for the food industry.

The present work shows that when mitochondrial beta-oxidation is stimulated by the hypolipemic, non-beta-oxidizable fattyacid analogue tetradecylthioacetic acid, there is a decrease in the secretion of triacylglycerol in cultured rat hepatocytes. In order to study the effects of tetradecylthioacetic acid in cells with different fattyacid oxidation rates, cells were grown without or with L-carnitine supplement or with addition of the beta-oxidation inhibitor L-aminocarnitine. In cells grown without and with L-carnitine in the medium, the oxidation of [1-14C]oleic acid was stimulated by tetradecylthioacetic acid, whereas it was not significantly changed by palmitic acid. In cells grown with L-aminocarnitine, oxidation of [1-14C]oleic acid was almost abolished both in the absence and in presence of tetradecylthioacetic acid. The effect of tetradecylthioacetic acid and palmitic acid on incorporation of [1-14C]oleic acid into triacylglycerol was similar under all conditions. In the presence of L-carnitine, secretion of oleic acid-labeled triacylglycerol was reduced significantly more by tetradecylthioacetic acid than by palmitic acid. The effects of tetradecylthioacetic acid and palmitic acid on secretion of oleic acid-labeled triacylglycerol were reversed in cells grown with L-aminocarnitine, where palmitic acid was the stronger inhibitor. These results were substantiated by determination of mass of triacylglycerol secreted. It is concluded that tetradecylthioacetic acid reduces secretion of triacylglycerol from rat hepatocytes mainly by acutely stimulating fattyacid oxidation.

Although the unsaturated fattyacid (UFA) synthetic pathway of Escherichia coli is the prototype of such pathways, several unresolved issues have accumulated over the years. The key players are the fabA and fabB genes. Earlier studies of fabA transcription showed that the gene was transcribed from two promoters, with one being positively regulated by the FadR protein. The other weaker promoter (which could not be mapped with the technology then available) was considered constitutive because its function was independent of FadR. However, the FabR negative regulator was recently shown to represses fabA transcription. We report that the weak promoter overlaps the FadR-dependent promoter and is regulated by FabR. This promoter is strictly conserved in all E. coli and Salmonella enterica genomes sequenced to date and is thought to provide insurance against inappropriate regulation of fabA transcription by exogenous saturated fattyacids. Also, the fabAup promoter, a mutant promoter previously isolated by selection for increased FabA activity, was shown to be a promoter created de novo by a four-base deletion within the gene located immediately upstream of fabA. Demonstration of the key UFA synthetic reaction catalyzed by FabB has been elusive, although it was known to catalyze an elongation reaction. Strains lacking FabB are UFA auxotrophs indicating that the enzyme catalyzes an essential step in UFA synthesis. Using thioesterases specific for hydrolysis of short chain acyl-ACPs, the intermediates of the UFA synthetic pathway have been followed in vivo for the first time. These experiments showed that a fabB mutant strain accumulated less cis-5-dodecenoic acid than the parental wild-type strain. These data indicate that the key reaction in UFA synthesis catalyzed by FabB is elongation of the cis-3-decenoyl-ACP produced by FabA. PMID:19679654

Oils were extracted from fully ripen Pinus pinea L. and Pinus halepensis Mill seeds and fattyacid composition has been established by capillary gas chromatography. Seeds are rich in lipids, 34.63-48.12% on a dry weight basis. Qualitatively, fattyacid composition of both species is identical. For P. halepensis linoleic acid is the major fattyacid (56.06% of total fattyacids) followed by oleic (24.03%) and palmitic (5.23%) acids. For P. pinea, the same fattyacids are found with the proportions 47.28%, 36.56%, and 6.67%, respectively. Extracted fattyacids from both species are mainly unsaturated, respectively, 89.87% and 88.01%. Pinus halepensis cis-5 olefinic acids are more abundant (7.84% compared to 2.24%). Results will be important as a good indication of the potential nutraceutical value of Pinus seeds as new sources of fruit oils rich in polyunsaturated fattyacids and cis-5 olefinic acids.

The group of conjugated fattyacids known as conjugated linoleic acid (CLA) isomers have been extensively studied with regard to their bioactive potential in treating some of the most prominent human health malignancies. However, CLA isomers are not the only group of potentially bioactive conjugated fattyacids currently undergoing study. In this regard, isomers of conjugated α-linolenic acid, conjugated nonadecadienoic acid and conjugated eicosapentaenoic acid, to name but a few, have undergone experimental assessment. These studies have indicated many of these conjugated fattyacid isomers commonly possess anti-carcinogenic, anti-adipogenic, anti-inflammatory and immune modulating properties, a number of which will be discussed in this review. The mechanisms through which these bioactivities are mediated have not yet been fully elucidated. However, existing evidence indicates that these fattyacids may play a role in modulating the expression of several oncogenes, cell cycle regulators, and genes associated with energy metabolism. Despite such bioactive potential, interest in these conjugated fattyacids has remained low relative to the CLA isomers. This may be partly attributed to the relatively recent emergence of these fattyacids as bioactives, but also due to a lack of awareness regarding sources from which they can be produced. In this review, we will also highlight the common sources of these conjugated fattyacids, including plants, algae, microbes and chemosynthesis.

Omega-3 and omega-6 fattyacids are polyunsaturated fattyacids (PUFAs) with multiple double bonds. Linolenic and alpha-linolenic acids are omega-6 and omega-3 PUFAs, precursors for the synthesis of long-chain PUFAs (LC-PUFAs), such as arachidonic acid (omega-6 PUFA), and eicosapentaenoic and docosahexaenoic acids (omega-3 PUFAs). The three most important omega-3 fattyacids are alpha-linolenic, eicosapentaenoic and docosahexaenoic acids, which cannot be synthesized in enough amounts by the body, and therefore they must be supplied by the diet. Omega-3 fattyacids are essential for the correct functioning of the organism and participate in many physiological processes in the brain. Epilepsy is a common and heterogeneous chronic brain disorder characterized by recurrent epileptic seizures leading to neuropsychiatric disabilities. The prevalence of epilepsy is high achieving about 1% of the general population. There is evidence suggesting that omega-3 fattyacids may have neuroprotective and anticonvulsant effects and, accordingly, may have a potential use in the treatment of epilepsy. In the present review, the potential use of omega-3 fattyacids in the treatment of epilepsy, and the possible proposed mechanisms of action are discussed. The present article summarizes the recent knowledge of the potential protective role of dietary omega-3 fattyacids in epilepsy.

The content of total lipids and the fattyacid (FA) profile were determined for eight macroalgae (Cystoseira abies-marina, Fucus spiralis, Chaetomorpha pachynema, Codium elisabethae, Porphyra sp., Osmundea pinnatifida, Pterocladiella capillacea and Sphaeroccoccus coronopifolius). Total lipids were extracted using a solvent mixture of methanol/chloroform (2/1, v/v) and further derivatised to FA methyl esters (FAME). The analyses of FAME samples were performed by gas chromatography coupled to a flame ionisation detector. The total lipid content ranged from 0.06 to 3.54 g (per 100 g). The most abundant saturated FA were palmitic (C16:0) and myristic (C14:0), while oleic (C18:1 n-9) was the dominant monounsaturated acid. All seaweeds contained linoleic FA (C18:2 n-6). The α-linolenic (C18:3 n-3) and eicosapentaenoic (20:5 n-3) acids were present only in Porphyra sp. (3.34% ± 0.13) and C. pachynema (0.47% ± 0.12), respectively. The n-6/n-3 and h/H ratios were low, suggesting a high nutritional value of the algae studied.

Maternal adipose tissue is a major contributor to breast milk long-chain fattyacids, probably through the pool of plasma NEFA. The fattyacid composition of the erythrocyte membrane (EM) is a biochemical index of the intake of fattyacids not synthesized endogenously and of PUFA and long-chain PUFA fattyacid status. The present study investigated the associations between breast milk fattyacid composition and the composition of plasma NEFA and of EM fattyacids with special reference to PUFA, long-chain PUFA and conjugated linoleic acid (CLA). The detailed fattyacid composition of mature breast milk was also reported. Thirty-three healthy, lactating Brazilian women donated milk samples; of these, twenty-four also donated blood samples in an observational cross-sectional study. Breast milk fattyacid composition presented several associations with NEFA and EM composition, which explained most (> or =50 %) of the variability of selected milk PUFA, long-chain PUFA and CLA. Milk CLA was associated with fattyacids that are markers of dairy fat intake in the diet, NEFA and EM. In general, breast milk n-3 fattyacids and CLA, but not n-6 fattyacids, were associated with EM composition, whereas both the n-6 and n-3 fattyacids and CLA in milk were associated with NEFA composition, possibly owing to its role as a direct source of fattyacids for breast milk. These findings emphasize the contribution of the NEFA pool derived from the adipose tissue to the long-chain fattyacid composition of breast milk.

The possibility of thiamine partaking in the synthesis of fattyacids through the functions unrelated to the catalytic properties of thiamine-diphosphate was studied. Rats kept on a fat-free ration devoid of thiamine were given thiamine of thiochrome with no vitaminic properties. The total fattyacids content in different tissues and incorporation therein of tagged acetate and pyruvate was determined, while the fattyacids composition of the liver was investigated by using gas chromatography. Thiamine and thiochrome produced a similar effect on a number of the study factors, i.e. they forced down the total acids level in the spleen, intensified incorporation of tagged acetate and pyruvate in fattyacids of the heart and uniformly changed the fattyacids composition in the liver. It is suggested that the unindirectional effects of thiamine and thiochrome is due to the oxidative transformation of thiamine into thiochrome.

The long hydrocarbon fatty acyl chain is energy rich, making it an ideal precursor for liquid transportation fuels and high-value oleo chemicals. As Saccharomyces cerevisiae has many advantages for industrial production compared to Escherichia coli. Here, we attempted to engineer Saccharomyces cerevisiae for overproduction of fattyacids. First, disruption of the beta-oxidation pathway, elimination of the acyl-CoA synthetases, overexpression of different thioesterases and acetyl-CoA carboxylase ACC1, and engineering the supply of precursor acetyl-CoA. The engineered strain XL122 produced more than 120 mg/L of fattyacids. In parallel, we inactivated ADH1, the dominant gene for ethanol production, to redirect the metabolic flux to fattyacids synthesis. The engineered strain DG005 produced about 140 mg/L fattyacids. Additionally, Acetyl-CoA carboxylase was identified as a critical bottleneck of fattyacids synthesis in S. cerevisiae with a cell-free system. However, overexpression of ACC1 has little effect on fattyacids biosynthesis. As it has been reported that phosphorylation of ACC1 may influent its activity, so phosphorylation sites of ACC1 were further identified. Although the regulatory mechanisms remain unclear, our results provide rationale for future studies to target this critical step. All these efforts, particularly the discovery of the limiting step are critical for developing a "cell factory" for the overproduction of fattyacids by using type I fattyacids synthase in yeast or other fungi.

Increased consumption of fatty fish, rich in omega-3-polyunsaturated fattyacids (ω3-PUFAs) reduces the severity and number of arrhythmias. Long-term ω3-PUFA-intake modulates the activity of several cardiac ion channels leading to cardiac action potential shortening. Circulating ω3-PUFAs in the bloodstream and incorporated ω3-PUFAs in the cardiac membrane have a different mechanism to shorten the action potential. It is, however, unknown whether circulating ω3-PUFAs in the bloodstream enhance or diminish the effects of incorporated ω3-PUFAs. In the present study, we address this issue. Rabbits were fed a diet rich in fish oil (ω3) or sunflower oil (ω9, as control) for 3 weeks. Ventricular myocytes were isolated by enzymatic dissociation and action potentials were measured using the perforated patch-clamp technique in the absence and presence of acutely administered ω3-PUFAs. Plasma of ω3 fed rabbits contained more free eicosapentaenoic acid (EPA) and isolated myocytes of ω3 fed rabbits contained higher amounts of both EPA and docosahexaenoic acid (DHA) in their sarcolemma compared to control. In the absence of acutely administered fattyacids, ω3 myocytes had a shorter action potential with a more negative plateau than ω9 myocytes. In the ω9 myocytes, but not in the ω3 myocytes, acute administration of a mixture of EPA + DHA shortened the action potential significantly. From these data we conclude that incorporated ω3-PUFAs into the sarcolemma and acutely administered ω3 fattyacids do not have a cumulative effect on action potential duration and morphology. As a consequence, patients with a high cardiac ω3-PUFA status will probably not benefit from short term ω3 supplementation as an antiarrhythmic therapy. PMID:21423389

The mechanism by which sex steroids influence very low density hepatic lipoprotein triglyceride production has not been fully elucidated. In previous studies we showed that [14C]oleate utilization and incorporation into triglycerides were greater in hepatocyte suspensions from adult female rats than from males. The sex differences were not related to activities of the enzymes of triglyceride biosynthesis, whereas fattyacid binding protein (FABP) concentration in liver cytosol was greater in females. These findings suggested that sex differences in lipoprotein could reflect a sex steroid influence on the availability of fattyacids for hepatocellular triglyceride biosynthesis. In the present studies, sex steroid effects on hepatocyte [14C]oleate utilization and FABP concentration were investigated directly. Hepatocytes from immature (30-d-old) rats exhibited no sex differences in [14C]oleate utilization. With maturation, total [14C]oleate utilization and triglyceride biosynthesis increased moderately in female cells and decreased markedly in male cells; the profound sex differences in adults were maximal by age 60 d. Fattyacid oxidation was little affected. Rats were castrated at age 30 d, and received estradiol, testosterone, or no hormone until age 60 d, when hepatocyte [14C]oleate utilization was studied. Castration virtually eliminated maturational changes and blunted the sex differences in adults. Estradiol or testosterone largely reproduced the appropriate adult pattern of [14C]oleate utilization regardless of the genotypic sex of the treated animal. In immature females and males, total cytosolic FABP concentrations were similar. In 60-d-old animals, there was a striking correlation among all groups (females, males, castrates, and hormone-treated) between mean cytosolic FABP concentration on the one hand, and mean total [14C]oleate utilization (r = 0.91) and incorporation into triglycerides (r = 0.94) on the other. In 30-d-old animals rates of [14C

In order to elucidate the biosynthesis of long-chain polyunsaturated fattyacids (PUFAs) in plants we searched for a cDNA encoding a Delta(6)-specific PUFA elongase from Physcomitrella patens, which is known to contain high proportions of arachidonic acid (20:4 Delta(5,8,11,14)). An EST clone from P. patens was identified by its low homology to the yeast gene ELO1, which is required for the elongation of medium-chain fattyacids. We functionally characterized this cDNA by heterologous expression in Saccharomyces cerevisiae grown in the presence of several fattyacids. Analysis of the fattyacid profile of the transgenic yeast revealed that the cDNA encodes a protein that leads to the elongation of the C(18) Delta(6)-polyunsaturated fattyacids gamma-linolenic acid (18:3 Delta(6,9,12)) and stearidonic acid (18:4 Delta(6,9,12,15)), which were recovered to 45-51% as their elongation products. In contrast, linoleic and alpha-linolenic acids were hardly elongated and we could not measure any elongation of saturated and mono-unsaturated fattyacids (including 18:1 Delta(6)), indicating that the elongase is highly specific for the polyunsaturated nature of the fattyacid acting as substrate.

Free fattyacids (FFA) content of beer affects the ability to form a stable head of foam and plays an important role in beer staling. Moreover, the presence of saturated FAs is related sometimes to gushing problems in beer. The aim of this research was to validate an analytical method for the determination of FFAs in beer. The extraction of FFAs in beer was achieved via Liquid-Liquid Cartridge Extraction (LLCE), the FFAs extract was purified by Solid Phase Extraction (SPE), methylated by boron trifluoride in methanol, and injected into GC-FID system. The performance criteria demonstrate that this method is suitable for the analysis of medium and long chain FFAs in beer. The proposed method was tested on four experimental beers.

To determine whether the composition of long-chain polyunsaturated fattyacids (PUFA) could be modified in the fetus by maternal dietary fattyacids, pregnant Sprague-Dawley rats were fed semipurified diets that differed only in the non-vitamin lipid component. The diets contained either 10 g palm, sunflower, olive or fish oil (FOD)/100 g diet. A total of 5-6 rats were studied in each group. At day 20 of gestation, corresponding to 1.5 days prior parturition, the fattyacids in maternal adipose tissue were closely related to the fattyacid composition in the corresponding diet. An important proportion of arachidonic acid (AA) appeared in maternal liver and plasma, although it was lower in the FOD than in the other groups. Except for saturated fattyacids, the proportion of individual fattyacids in the placenta correlated linearly with that in maternal plasma. Also, PUFA in fetal plasma and liver showed significant correlations with PUFA in maternal plasma. Again, AA showed the lowest proportion in the plasma and liver of the FOD group. Therefore, the maternal dietary fattyacid composition influences maternal and fetal plasma and tissue composition, and an increase in dietary omega-3 fattyacids decreases the amount of AA in maternal and fetal tissues.

Microbial production of fats and oils is being developedas a means of converting biomass to biofuels. Here we investigate enhancing expression of enzymes involved in the production of fattyacids and triglycerides as a means to increase production of these compounds in Aspergillusoryzae. Examination of the A.oryzaegenome demonstrates that it contains twofatty acid synthases and several other genes that are predicted to be part of this biosynthetic pathway. We enhancedthe expressionof fattyacid synthesis-related genes by replacing their promoters with thepromoter fromthe constitutively highly expressedgene tef1. We demonstrate that by simply increasing the expression of the fattyacid synthasegenes we successfullyincreasedtheproduction of fattyacids and triglyceridesby more than two fold. Enhancement of expression of the fattyacid pathway genes ATP-citrate lyase and palmitoyl-ACP thioesteraseincreasedproductivity to a lesser extent.Increasing expression ofacetyl-CoA carboxylase caused no detectable change in fattyacid levels. Increases in message level for each gene were monitored usingquantitative real-time RT-PCR. Our data demonstrates that a simple increase in the abundance of fattyacid synthase genes can increase the detectable amount of fattyacids.

Freshwater green algae Rhizoclonium hieroglyphicum growing in the Ural Mountains were examined for their fattyacid amides using capillary gas chromatography-mass spectrometry (GC-MS). Eight fattyacid amides were identified by GC-MS. (Z)-9-octadecenamide was found to be the major component (2.26%).

Fattyacid alkyl esters of plant oils, especially in the form of methyl esters, have numerous applications with fuel use having received the most attention in recent times due to the potential high volume. Various properties imparted by neat fattyacid alkyl esters have been shown to influence fuel ...

Well over 1,000 different fattyacids are known which are natural components of fats, oils (triacylglycerols), and other related compounds. These fattyacids can have different alkyl chain lengths, 0-6 carbon-carbon double bonds possessing cis- or trans-geometry, and can contain a variety of functio...

saturated fattyacids ) were explored to determine the relationship of the detergencies of such systems to the physico-chemical nature (HLB, hydrophile...suggested that in such systems the chief action is van der Waals adsorption between hydr oxide mole ratio adducts of tridecyl alcohol are poor detergents of the saturated fattyacids .

This study reports the fattyacid profiles of 25 alternative lipid feedstocks for the production of bio-based fuels and chemicals. Lipids were extracted using hexane from oil-bearing seeds using a standard Soxhlet apparatus. Fattyacid profiles were measured using gas chromatography-flame ionization...

Fattyacids are primary metabolites synthesized by complex, elegant, and essential biosynthetic machinery. Fattyacid synthases resemble an iterative assembly line, with an acyl carrier protein conveying the growing fattyacid to necessary enzymatic domains for modification. Each catalytic domain is a unique enzyme spanning a wide range of folds and structures. Although they harbor the same enzymatic activities, two different types of fattyacid synthase architectures are observed in nature. During recent years, strained petroleum supplies have driven interest in engineering organisms to either produce more fattyacids or specific high value products. Such efforts require a fundamental understandingmore » of the enzymatic activities and regulation of fattyacid synthases. Despite more than one hundred years of research, we continue to learn new lessons about fattyacid synthases' many intricate structural and regulatory elements. Lastly, in this review, we summarize each enzymatic domain and discuss efforts to engineer fattyacid synthases, providing some clues to important challenges and opportunities in the field.« less

Background: Synergistic and/or additive effects on cardiometabolic risk may be missed by examining individual fattyacids (FA). A pattern analysis may be a more useful approach. As well, it remains unclear whether erythrocyte fattyacid composition relates to insulin resistance among Hispanic/Latino...

As part of a study of the seed oil fattyacid composition of Malvaceae plants, seeds of seven Tilia species (limes or linden trees) were evaluated for their fattyacid profiles. Seeds were obtained from the Germplasm Research Information Network and from various commercial sources. After extractio...

Background Direct conversion of solar energy and carbon dioxide to drop in fuel molecules in a single biological system can be achieved from fattyacid-based biofuels such as fatty alcohols and alkanes. These molecules have similar properties to fossil fuels but can be produced by photosynthetic cyanobacteria. Results Synechocystis sp. PCC6803 mutant strains containing either overexpression or deletion of the slr1609 gene, which encodes an acyl-ACP synthetase (AAS), have been constructed. The complete segregation and deletion in all mutant strains was confirmed by PCR analysis. Blocking fattyacid activation by deleting slr1609 gene in wild-type Synechocystis sp. PCC6803 led to a doubling of the amount of free fattyacids and a decrease of alkane production by up to 90 percent. Overexpression of slr1609 gene in the wild-type Synechocystis sp. PCC6803 had no effect on the production of either free fattyacids or alkanes. Overexpression or deletion of slr1609 gene in the Synechocystis sp. PCC6803 mutant strain with the capability of making fatty alcohols by genetically introducing fatty acyl-CoA reductase respectively enhanced or reduced fatty alcohol production by 60 percent. Conclusions Fattyacid activation functionalized by the slr1609 gene is metabolically crucial for biosynthesis of fattyacid derivatives in Synechocystis sp. PCC6803. It is necessary but not sufficient for efficient production of alkanes. Fatty alcohol production can be significantly improved by the overexpression of slr1609 gene. PMID:22433663

Inhibitory effect of 44 species of fattyacids on cholesterol synthesis has been examined with a rat liver enzyme system. In the case of saturated fattyacids, the inhibitory activity increased with chain length to a maximum at 11 to 14 carbons, after which activity decreased rapidly. The inhibition increased with the degree of unsaturation of fattyacids. Introduction of a hydroxy group at the alpha-position of fattyacids abolished the inhibition, while the inhibition was enhanced by the presence of a hydroxy group located in an intermediate position of the chain. Branched chain fattyacids having a methyl group at the terminal showed much higher activity than the corresponding saturated straight chain fattyacids with the same number of carbons. With respect to the mechanism for inhibition, tridecanoate was found to inhibit acetoacetyl-CoA thiolase specifically without affecting the other reaction steps in the cholesterol synthetic pathway. The highly unsaturated fattyacids, arachidonate and linoleate, were specific inhibitors of 3-hydroxy-3-methyl-glutaryl-CoA synthase. On the other hand, ricinoleate (hydroxy acid) and phytanate (branched-chain acid) diminished the conversion of mevalonate to sterols by inhibiting a step or steps between squalene and lanosterol.

The influence of dietary omega-3 fattyacids on health outcomes is widely recognized. The adequate intake of omega-3 fattyacids docasahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) in particular can increase gestation length and improve infant cognitive and visual performance. Adequate levels of omega-3 fattyacids have also been shown to reduce the incidence of preterm birth in some populations. Research on prenatal omega-3 intake and other outcomes, such as preeclampsia and fetal growth restriction, is inconclusive. Women in the United States consume low levels of omega-3 fattyacids compared to omega-6 fattyacids; this dietary pattern is associated with poor health outcomes. Omega-3 fattyacids are found primarily in fish, yet many pregnant women avoid fish because of concerns about potential mercury and polychlorinated biphenyl contamination. It is important for prenatal care providers to assess women's diets for omega-3 fattyacid intake and ensure that pregnant women are consuming between 200 and 300 mg daily from safe food sources. Purified fish, algal oil supplements, and DHA-enriched eggs are alternative sources for pregnant women who do not eat fish.

Deinococcus radiodurans contains novel phospholipids of which the structures of three have been previously described. These three lipids contain both fattyacids and alkylamines. Both the fattyacid and alkylamine constituents were found to be composed of a mixture of species, of which C15, C16, and C17 saturated and monounsaturated alkyl chains predominated. Alkylamines contained a relatively higher proportion of saturated species. Progression of bacterial growth through the mid-log to stationary phases was accompanied by an increase in the proportions of C15 and C17 alkyl chains in both fattyacid and alkylamine constituents. Radiolabeled palmitic acid was found to be rapidly incorporated into both fattyacid and alkylamine components of phosphatidylglyceroylalkylamine, which is the precursor of the more-complex phosphoglycolipids found in major amounts in D. radiodurans. After culturing D. radiodurans in the presence of a mixture of palmitic acids labeled with 14C and 3H in the 1 and 9,10 positions, respectively, the same 14C/3H ratio was recovered in both fattyacid and alkylamine constituents, strongly suggesting that alkylamines are derived from intact fattyacids rather than by a de novo pathway. The results identify a novel product of fattyacid metabolism which has not to date been observed in any other organism. Images PMID:1429439

1. Radioactivity from cyclopropane[14C]carboxylic acid is incorporated into fattyacids in vitro by rat and guinea-pig adipose tissue, by rat liver slices and by the supernatant fraction of rat liver homogenate. 2. The labelled acids are different from endogenous straight-chain fattyacids, and evidence is produced that they consist of a cyclopropyl ring in the ω-position, the remainder of the chain being built up from C2 units (not derived from cyclopropanecarboxylic acid) in the normal way via the malonate pathway. 3. It is suggested that these unnatural acids have some metabolic effect related to the hypoglycaemic action of cyclopropanecarboxylic acid. PMID:5685874

Background As an alternative for economic biodiesel production, the microbial production of extracellular fattyacid from renewable resources is receiving more concerns recently, since the separation of fattyacid from microorganism cells is normally involved in a series of energy-intensive steps. Many attempts have been made to construct fattyacid producing strains by targeting genes in the fattyacid biosynthetic pathway, while few studies focused on the cultivation process and the mass transfer kinetics. Results In this study, both strain improvements and cultivation process strategies were applied to increase extracellular fattyacid production by engineered Escherichia coli. Our results showed overexpressing ‘TesA and the deletion of fadL in E. coli BL21 (DE3) improved extracellular fattyacid production, while deletion of fadD didn’t strengthen the extracellular fattyacid production for an undetermined mechanism. Moreover, the cultivation process controls contributed greatly to extracellular fattyacid production with respect to titer, cell growth and productivity by adjusting the temperature, adding ampicillin and employing on-line extraction. Under optimal conditions, the E. coli strain (pACY-‘tesA-ΔfadL) produced 4.8 g L−1 extracellular fattyacid, with the specific productivity of 0.02 g h−1 g−1dry cell mass, and the yield of 4.4% on glucose, while the ratios of cell-associated fattyacid versus extracellular fattyacid were kept below 0.5 after 15 h of cultivation. The fattyacids included C12:1, C12:0, C14:1, C14:0, C16:1, C16:0, C18:1, C18:0. The composition was dominated by C14 and C16 saturated and unsaturated fattyacids. Using the strain pACY-‘tesA, similar results appeared under the same culture conditions and the titer was also much higher than that ever reported previously, which suggested that the supposedly superior strain did not necessarily perform best for the efficient production of desired product. The strain p

Several studies have aimed to unravel the contribution of different types of dietary fattyacids to human health and disease. Investigations have consistently shown that high consumption of industrially produced trans-fattyacids from partially hydrogenated vegetable oils is harmful to human health, in particular cardiovascular health. Therefore, the U.S. Food and Drug Administration announced that partially hydrogenated oils are no longer 'generally recognized as safe', and trans-fattyacids are not permitted in the U.S. food supply. On the other hand, recent studies analyzing the association between circulating trans-fattyacids and disease have revealed that some ruminant-specific trans-fattyacids are associated with a reduction in incidence of disease. In this special report, we highlight recent findings and point out perspectives for future studies on this topic.

Neutrophils are well-known to act in the destruction of invading microorganisms. They have also been implicated in the activation of other immune cells including B- and T-lymphocytes and in the resolution of inflammation and tissue regeneration. Neutrophils are produced in the bone marrow and released into the circulation from where they migrate to tissues to perform their effector functions. Neutrophils are in constant contact with fattyacids that can modulate their function, activation and fate (survival or cell death) through different mechanisms. In this review, the effects of fattyacids pertaining to five classes, namely, long-chain saturated fattyacids (LCSFAs), short-chain fattyacids (SCFAs), and omega-3 (n-3), omega-6 (n-6) and omega-9 (n-9) unsaturated fattyacids, on neutrophils and the relevance of these effects for disease development are discussed.

The moisture and lipid content as well as the fattyacid composition of sausages were determined. Lipids were extracted and purified with a mixture of cloroform/methanol 2:1. Fattyacids in the lipid extract were methylated with 4% sulfuric acid/methanol solution and later were separated as methyl esters by gas liquid cromatography (GLC). Sausages presented a lipid content between 7.10% for canned sausages and 35.23% for the cocktail type. Most of the fattyacids were monounsatured with oleic acid as the major component with values between 42.54% for ham sausage and 48.83% for francfort type. Satured fattyacids followed, with palmitic acid as the major component in a range between 21.46% and 26.59% for bologna and Polaca sausage respectively. Polyunsaturated fattyacids were present in less quantities with concentration of linoleic acid between 8.5% (cotto salami type) and 12.60% (cocktail type). Turkey and poultry sausages presented a higher content of polyunsaturated and less saturated fattyacids than the other types of sausages studied.

GC-MS investigations were carried out to elucidate the aging behavior of unsaturated fattyacids in fingerprint residues and to identify their degradation products in aged samples. For this purpose, a new sample preparation technique for fingerprint residues was developed that allows producing N-methyl-N-trimethylsilyl-trifluoroacetamide (MSTFA) derivatives of the analyzed unsaturated fattyacids and their degradation products. MSTFA derivatization catalyzed by iodotrimethylsilane enables the reliable identification of aldehydes and oxoacids as characteristic MSTFA derivatives in GCMS. The obtained results elucidate the degradation pathway of unsaturated fattyacids. Our study of aged fingerprint residues reveals that decanal is the main degradation product of the observed unsaturated fattyacids. Furthermore, oxoacids with different chain lengths are detected as specific degradation products of the unsaturated fattyacids. The detection of the degradation products and their chain length is a simple and effective method to determine the double bond position in unsaturated compounds. We can show that the hexadecenoic and octadecenoic acids found in fingerprint residues are not the pervasive fattyacids Δ9-hexadecenoic (palmitoleic acid) and Δ9-octadecenoic (oleic acid) acid but Δ6-hexadecenoic acid (sapienic acid) and Δ8-octadecenoic acid. The present study focuses on the structure identification of human sebum-specific unsaturated fattyacids in fingerprint residues based on the identification of their degradation products. These results are discussed for further investigations and method developments for age determination of fingerprints, which is still a tremendous challenge because of several factors affecting the aging behavior of individual compounds in fingerprints. Graphical Abstract ᅟ.

GC-MS investigations were carried out to elucidate the aging behavior of unsaturated fattyacids in fingerprint residues and to identify their degradation products in aged samples. For this purpose, a new sample preparation technique for fingerprint residues was developed that allows producing N-methyl- N-trimethylsilyl-trifluoroacetamide (MSTFA) derivatives of the analyzed unsaturated fattyacids and their degradation products. MSTFA derivatization catalyzed by iodotrimethylsilane enables the reliable identification of aldehydes and oxoacids as characteristic MSTFA derivatives in GCMS. The obtained results elucidate the degradation pathway of unsaturated fattyacids. Our study of aged fingerprint residues reveals that decanal is the main degradation product of the observed unsaturated fattyacids. Furthermore, oxoacids with different chain lengths are detected as specific degradation products of the unsaturated fattyacids. The detection of the degradation products and their chain length is a simple and effective method to determine the double bond position in unsaturated compounds. We can show that the hexadecenoic and octadecenoic acids found in fingerprint residues are not the pervasive fattyacids Δ9-hexadecenoic (palmitoleic acid) and Δ9-octadecenoic (oleic acid) acid but Δ6-hexadecenoic acid (sapienic acid) and Δ8-octadecenoic acid. The present study focuses on the structure identification of human sebum-specific unsaturated fattyacids in fingerprint residues based on the identification of their degradation products. These results are discussed for further investigations and method developments for age determination of fingerprints, which is still a tremendous challenge because of several factors affecting the aging behavior of individual compounds in fingerprints.

dehydrogenation of fattyacids Contract/Grant#: FA9550-10-1-0532 Final Reporting Period: 15 September 2011 to 14 September 2011...directly incorporate fattyacids into the ligand. The preparation of the acyl phosphines (1-5) was easily accomplished starting from the corresponding...AFOSR Final Report Final Report The proposed research examines the site-selective dehydrogenation of alkanes. The alkanes employed were fatty

Catalyst preparation and characterization of Al3+-bentonite for esterification of palmitic acid, oleic acid and linoleic acid has been done. Al3+-bentonite catalyst was prepared from natural bentonite of Turen Malang through cation exchange reaction using AlCl3 solution. The catalysts obtained were characterized by XRD, XRF, pyridine-FTIR and surface area analyser using the BET method. Catalyst activity test of Al3+-bentonite for esterification reaction was done at 65°C using molar ratio of metanol-fattyacid of 30:1 and 0.25 g of Al3+-bentonite catalyst for the period of ½, 1, 2, 3, 4 and 5 hours. Based on the characterization results, the Al3+-bentonite Turen Malang catalyst has a d-spacing of 15.63 Ǻ, acid sites of Brönsted and Lewis respectively of 230.79 µmol/g and 99.39 µmol/g, surface area of 507.3 m2/g and the average of radius pore of 20.09 Å. GC-MS analysis results of the oil phase after esterification reaction showed the formation of biodiesel (FAME: Fattyacid methyl ester), namely methyl palmitate, methyl oleate and methyl linoleate. The number of conversions resulted in esterification reaction using Al3+-bentonite Turen Malang catalyst was 74.61%, 37.75%, and 20, 93% for the esterification of palmitic acid, oleic acid and linoleic acid respectively.

Indonesia, as one of the biggest palm oil producers and exporters in the world, is producing large amounts of low-grade oil such as Palm FattyAcid Distillate (PFAD) from palm oil industries. The use of PFAD can reduce the cost of biodiesel production significantly, which makes PFAD a highly potential alternative feedstock for biodiesel production. In this paper, the esterification of free fattyacid (FFA) on PFAD was studied using rice husk ash (RHA) as heterogeneous catalyst. The rice husk ash catalyst was synthesized by sulfonation using concentrated sulfuric acid. The RHA catalyst were characterized by using different techniques, such as porosity analysis, Fourier transform infrared (FT-IR) spectroscopy, total number of acid sites and elemental analysis. The effects of the molar ratio of methanol to PFAD (1-10%), the molar ratio of methanol to PFAD (4:1-10:1), and the reaction temperature (40-60°C) were studied for the conversion of FFA to optimize the reaction conditions. The results showed that the optimal conditions were an methanol to PFAD molar ratio of 10:1, the catalyst amount of 10 wt% of PFAD, and reaction temperature of 60°C.

An altered one-carbon cycle is known to influence placental and fetal development. We hypothesize that deficiency of maternal micronutrients such as folic acid and vitamin B12 will lead to increased oxidative stress, reduced long-chain polyunsaturated fattyacids, and altered expression of peroxisome proliferator activated receptor (PPARγ) in the placenta, and omega-3 fattyacid supplementation to these diets will increase the expression of PPARγ. Female rats were divided into 5 groups: control, folic acid deficient, vitamin B12 deficient, folic acid deficient + omega-3 fattyacid supplemented, and vitamin B12 deficient + omega-3 fattyacid supplemented. Dams were dissected on gestational day 20. Maternal micronutrient deficiency leads to lower (p < 0.05) levels of placental docosahexaenoic acid, arachidonic acid, PPARγ expression and higher (p < 0.05) levels of plasma malonidialdehyde, placental IL-6, and TNF-α. Omega-3 fattyacid supplementation to a vitamin B12 deficient diet normalized the expression of PPARγ and lowered the levels of placental TNF-α. In the case of supplementation to a folic acid deficient diet it lowered the levels of malonidialdehyde and placental IL-6 and TNF-α. This study has implications for fetal growth as oxidative stress, inflammation, and PPARγ are known to play a key role in the placental development.

Understanding the key aspects of the pathogenesis of alcoholic fatty liver disease particularly alterations to mitochondrial function remains to be resolved. The role of fattyacids in this regard requires further investigation due to their involvement in fatty liver disease and obesity. This study aimed to characterize the early effects of saturated and unsaturated fattyacids alone on liver mitochondrial function and during concomitant ethanol exposure using isolated liver mitochondria and VA-13 cells (Hep G2 cells that efficiently express alcohol dehydrogenase). Liver mitochondria or VA-13 cells were treated with increasing concentrations of palmitic or arachidonic acid (1 to 160 μM) for 24 h with or without 100 mM ethanol. The results showed that in isolated liver mitochondria both palmitic and arachidonic acids significantly reduced state 3 respiration in a concentration-dependent manner (P<0.001), implicating their ionophoric activities. Increased ROS production occurred in a dose-dependent manner especially in the presence of rotenone (complex I inhibitor), which was significantly more prominent in arachidonic acid at 80 μM (+970%, P<0.001) than palmitic acid (+40%, P<0.01). In VA-13 cells, ethanol alone and both fattyacids (40 μM) were able to decrease the mitochondrial membrane potential and cellular ATP levels and increase lipid formation. ROS production was significantly increased with arachidonic acid (+110%, P<0.001) exhibiting a greater effect than palmitic acid (+39%, P<0.05). While in the presence of ethanol, the drop in the mitochondrial membrane potential, cellular ATP levels, and increased lipid formation were further enhanced by both fattyacids, but with greater effect in the case of arachidonic acid, which also correlated with significant cytotoxicity (P<0.001). This study confirms the ability of fattyacids to promote mitochondrial injury in the development of alcoholic fatty liver disease.

Reverse phase high pressure liquid chromatography (HPLC) on octadecylsilyl columns separates mixtures of either free fattyacids or fattyacid methyl esters prepared from mammalian tissue phospholipids. Acetonitrile-water mixtures are used for the elution of esters. Aqueous phosphoric acid is substituted for water for the separation of the free acids. Unsaturated compounds are detected and quantitated by their absorption at 192 nm. Saturates are detected better at 205 nm. The order of elution of fattyacids in complex mixtures varies as a function of acetonitrile concentration. At any given concentration, some compounds overlap. However, by varying the solvent strength, any fattyacid of interest can be resolved including many geometrical and positional isomers. Methyl esters prefractionated according to unsaturation by argentation thin-layer chromatography (TLC) are rapidly and completely separated by elution with CH3CN alone. Argentation TLC-reverse phase HPLC can be used as an analytical as well as a preparative procedure. Octylsilyl columns are used for rapid resolution and improved detection of minor or low ultraviolet-absorbing components in the fractions. For example, monoenoic fattyacids with up to 32 carbons have been detected in bovine brain glycerophospholipids. Specific radioactivities of 3H- and 14C-labeled fattyacids and the distribution of radioactivity among acyl groups from complex lipids are measured. The method is not recommended for complete compositional analysis, but is useful for determinations of specific radioactivities during studies on turnover and metabolic conversions of labeled fattyacids.

This report describes the synthesis and preliminary biological characterization of novel fattyacid niacin conjugates and fattyacid salicylate conjugates. These molecular entities were created by covalently linking two bioactive molecules, either niacin or salicylic acid, to an omega-3 fattyacid. This methodology allows the simultaneous intracellular delivery of two bioactives in order to elicit a pharmacological response that could not be replicated by administering the bioactives individually or in combination. The fattyacid niacin conjugate 5 has been shown to be an inhibitor of the sterol regulatory element binding protein (SREBP), a key regulator of cholesterol metabolism proteins such as PCSK9, HMG-CoA reductase, ATP citrate lyase, and NPC1L1. On the other hand, the fattyacid salicylate conjugate 11 has been shown to have a unique anti-inflammatory profile based on its ability to modulate the NF-κB pathway through the intracellular release of the two bioactives.

Human beings evolved consuming a diet that contained about equal amounts of n-3 and n-6 essential fattyacids. Over the past 100-150 y there has been an enormous increase in the consumption of n-6 fattyacids due to the increased intake of vegetable oils from corn, sunflower seeds, safflower seeds, cottonseed, and soybeans. Today, in Western diets, the ratio of n-6 to n-3 fattyacids ranges from approximately 20-30:1 instead of the traditional range of 1-2:1. Studies indicate that a high intake of n-6 fattyacids shifts the physiologic state to one that is prothrombotic and proaggregatory, characterized by increases in blood viscosity, vasospasm, and vasoconstriction and decreases in bleeding time. n-3 Fattyacids, however, have antiinflammatory, antithrombotic, antiarrhythmic, hypolipidemic, and vasodilatory properties. These beneficial effects of n-3 fattyacids have been shown in the secondary prevention of coronary heart disease, hypertension, type 2 diabetes, and, in some patients with renal disease, rheumatoid arthritis, ulcerative colitis, Crohn disease, and chronic obstructive pulmonary disease. Most of the studies were carried out with fish oils [eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)]. However, alpha-linolenic acid, found in green leafy vegetables, flaxseed, rapeseed, and walnuts, desaturates and elongates in the human body to EPA and DHA and by itself may have beneficial effects in health and in the control of chronic diseases.

The establishment of renewable biofuel and chemical production is desirable because of global warming and the exhaustion of petroleum reserves. Sebacic acid (decanedioic acid), the material of 6,10-nylon, is produced from ricinoleic acid, a carbon-neutral material, but the process is not eco-friendly because of its energy requirements. Laccase-catalyzing oxidative cleavage of fattyacid was applied to the production of dicarboxylic acids using hydroxy and oxo fattyacids involved in the saturation metabolism of unsaturated fattyacids in Lactobacillus plantarum as substrates. Hydroxy or oxo fattyacids with a functional group near the carbon-carbon double bond were cleaved at the carbon-carbon double bond, hydroxy group, or carbonyl group by laccase and transformed into dicarboxylic acids. After 8 h, 0.58 mM of sebacic acid was produced from 1.6 mM of 10-oxo-cis-12,cis-15-octadecadienoic acid (αKetoA) with a conversion rate of 35% (mol/mol). This laccase-catalyzed enzymatic process is a promising method to produce dicarboxylic acids from biomass-derived fattyacids.

Adrenal glomerulosa cells washed with delipidated albumin produced increased amounts of aldosterone in response to angiotensin-II (AII) or (Bu)2cAMP. Albumin treatment also increased binding of 125I-labeled AII to high affinity binding sites on adrenal cells. Lipid extracts of albumin solutions that were used to wash cells inhibited AII binding and aldosterone responses by washed glomerulosa cells. Chromatographic fractionation and mass spectroscopic analysis indicated that the inhibitors removed from cells by albumin were long chain fattyacids. Exogenous fattyacids not only inhibited AII binding, but they inhibited basal aldosterone production and increments in aldosterone caused by AII or dbcAMP, suggesting an effect on postreceptor steps in aldosteronogenesis. The most potent and most abundant fattyacids removed from adrenal cells were oleic, linoleic, and arachidonic. These fattyacids inhibited at micromolar concentrations in the absence of albumin and at somewhat higher concentrations in its presence. Cells that had been washed, then inhibited by exogenous oleic acid in vitro, were restored to their enhanced responsiveness by a second albumin wash, making it unlikely that cell damage is the mechanism of inhibition by fattyacids. Responses of fasciculata cells were not potentiated by albumin washes, and cortisol production was less sensitive than aldosterone production to exogenous fattyacids. Binding of ANP to glomerulosa cells was not affected by albumin or fattyacids. These results combined with clinical correlations make it plausible that unesterified fattyacids are naturally occurring regulators of the adrenal glomerulosa. Insulin's ability to lower plasma levels of fattyacids may be one way that it causes sodium retention.

the longer fattyacids, palmitic acid, stearic acid, oleic acid and Tween 80 showed good growth. Growth was so intense in the case of palmitic acid and...longer permitted reproduction. Most favorable were oleic acid in concentrations of .0001 m and . 00001 m, stearic and palmitic acid at .0001. Tween ... 80 gave good growth, but only in the presence of gelatin, in concentrations of 28.2 to 0.00282 mg%. The best results were achieved at higher concentrations of 28.2 and 2.82 mg%. More than 100 organisms were counted in the field.

A study is conducted to determine the amino acid, fattyacid, and carbohydrate content of breadfruit using high-performance liquid chromatography (HPLC) and gas chromatography (GC). An HPLC method is used for the determination of amino acids and fattyacids in breadfruit. Representative amino acid samples are derivatized with phenylisothiocianate and the resulting phenylthiocarbamyl derivatives are separated on a reversed-phase column by gradient elution with a 0.05M ammonium acetate buffer and 0.01M ammonium acetate in acetonitrile-methanol-water (44:10:46, v/v). Representative fattyacid samples are derivatized with phenacyl bromide and the resulting fattyacid phenacyl esters are separated on a reversed-phase column by gradient elution with acetonitrile and water. Amino acid and fattyacid derivatives are detected by ultraviolet detection at 254 nm. The analysis of the carbohydrates in breadfruit employs a GC method. Carbohydrates are derivatized using trimethylchlorosilane and hexamethyldisilazane to form trimethylsilyl ethers. Compounds in the samples are separated by the temperature programming of a GC using nitrogen as the carrier gas. Percent recoveries of amino acids, fattyacids, and carbohydrates are 72.5%, 68.2%, and 81.4%, respectively. The starch content of the breadfruit is 15.52 g/100 g fresh weight.

Diets rich in saturated fattyacids have long been associated with increased plasma cholesterol concentrations and hence increased risk of cardiovascular disease. More recently, they have also been suggested to promote the development of non-alcoholic fatty liver disease. While there is now considerable evidence to suggest that polyunsaturated fattyacids exert many of their effects through regulating the activity of transcription factors, including peroxisome proliferator activated receptors, sterol regulatory binding proteins (SREBPs) and liver X receptor, our understanding of how saturated fattyacids act is still limited. Here we review the potential mechanisms whereby saturated fattyacids modulate hepatic lipid metabolism thereby impacting on the synthesis, storage and secretion of lipids. Evidence is presented that their effects are, at least partly, mediated through modulation of the activity of the SREBP family of transcription factors.

Primary fattyacid amides are a group of biologically highly active compounds which were already identified in nature. Here, these substances were determined in tallow and tallow fattyacid methyl esters for the first time. As tallow is growing in importance as an oleochemical feedstock for the soap manufacturing, the surfactant as well as the biodiesel industry, the amounts of primary fattyacid amides have to be considered. As these compounds are insoluble in tallow as well as in the corresponding product e.g. tallow fattyacid methyl esters, filter plugging can occur. For the quantification in these matrices a purification step and a LC-APCI-MS method were developed. Although quantification of these compounds can be performed by GC-MS, the presented approach omitted any derivatization and increased the sensitivity by two orders of magnitude. Internal standard calibration using heptadecanoic acid amide and validation of the method yielded a limit of detection of 18.5 fmol and recoveries for the tallow and fattyacid methyl ester matrices of 93% and 95%, respectively. A group of commercially available samples were investigated for their content of fattyacid amides resulting in an amount of up to 0.54%m/m (g per 100 g) in tallow and up to 0.16%m/m (g per 100 g) in fattyacid methyl esters.

Phagocytosis is an early and fundamental step for the effective clearance of disease causing agents. The ability to engulf and kill pathogens is considered as a major effector function of macrophages. In their phagocytic role macrophages are part of the first line of innate immune defense. A number of studies investigating fattyacid effects on macrophage phagocytosis have been conducted over many years. In vitro-data consistently report that alterations in macrophage membrane fattyacid composition are linked to an altered phagocytic capacity, i.e. an increase in membrane unsaturated fattyacid content is associated with an increase in engulfment and killing rate. The mode of action of fattyacids seems to be the modulation of the physical nature of the macrophage plasma membrane. It appears that the saturated-to-unsaturated fattyacid ratio of macrophage membrane phospholipids is of importance in determining macrophage phagocytic capacity. Available in vivo-data are less clear. At present, there is a lack of systematic studies elucidating key factors such as fattyacid efficacy, effective dose or dosing intervals. Without this knowledge the targeted modulation of macrophage phagocytosis in vivo by fattyacids is still a distant possibility.

Saw palmetto supplements are one of the most commonly consumed supplements by men with prostate cancer and/or benign prostatic hyperplasia (BPH). Some studies have found significant improvements in BPH and lower urinary tract symptoms (LUTS) with saw palmetto supplementation, whereas others found no benefits. The variation in the efficacy in these trials may be a result of differences in the putative active components, fattyacids and phytosterols, of the saw palmetto supplements. To this end, we quantified the major fattyacids (laurate, myristate, palmitate, stearate, oleate, linoleate) and phytosterols (campesterol, stigmasterol, β-sitosterol) in 20 commercially available saw palmetto supplements using GC-FID and GC-MS, respectively. Samples were classified into liquids, powders, dried berries, and tinctures. Liquid saw palmetto supplements contained significantly higher (p < 0.05) concentrations of total fattyacids (908.5 mg/g), individual fattyacids, total phytosterols (2.04 mg/g), and individual phytosterols, than the other supplement categories. Powders contained significantly higher (p < 0.05) concentrations of total fattyacids than tinctures, which contain negligible amounts of fattyacids (46.3 mg/g) and phytosterols (0.10 mg/g). Our findings suggest that liquid saw palmetto supplements may be the best choice for individuals who want to take a saw palmetto supplement with the highest concentrations of both fattyacids and phytosterols.

The toxicity of fattyacid salts to German, Blattella germanica (L.), and American cockroaches, Periplaneta americana (L.), was evaluated. Potassium and sodium laurate caused up to 95% mortality of German cockroaches and 100% mortality of American cockroaches. Even-numbered potassium fattyacid salts, C8-C18 were assessed for toxicity at 0.125, 0.25, 0.5, 1, and 2% concentrations by a 30-s immersion of cockroaches. The more soluble of the fattyacid salts at 2% concentration caused 65-95% mortality of German cockroaches and 100% mortality of American cockroaches. Potassium oleate, C18, was most toxic to both German (LC50 = 0.36%) and American (LC50 = 0.17%) cockroaches. Fattyacid salt solutions on a substrate were tested by placing cockroaches in contact with treated floor tiles immediately after application (wet) or after the solutions had dried. Sodium laurate and potassium caprate caused mortality of German (62 +/- 17.4 and 58 +/- 12.6%, respectively) and American cockroaches (52 +/- 18.5 and 28 +/- 4.9%, respectively) on wet tiles, whereas potassium oleate caused mortality of German cockroaches (67 +/- 14.1%) only. Dry fattyacids caused no mortality among exposed cockroaches. Fattyacid salt solutions can be effective in killing German and American cockroaches but only when insects are thoroughly wetted with 1-2% fattyacid salt solutions.

Saw palmetto supplements are one of the most commonly consumed supplements by men with prostate cancer and/or benign prostatic hyperplasia (BPH). Some studies have found significant improvements in BPH and lower urinary tract symptoms (LUTS) with saw palmetto supplementation, whereas others found no benefits. The variation in the efficacy in these trials may be a result of differences in the putative active components, fattyacids and phytosterols, of the saw palmetto supplements. To this end, we quantified the major fattyacids (laurate, myristate, palmitate, stearate, oleate, linoleate) and phytosterols (campesterol, stigmasterol, β-sitosterol) in 20 commercially available saw palmetto supplements using GC-FID and GC-MS, respectively. Samples were classified into liquids, powders, dried berries, and tinctures. Liquid saw palmetto supplements contained significantly higher (p < 0.05) concentrations of total fattyacids (908.5 mg/g), individual fattyacids, total phytosterols (2.04 mg/g), and individual phytosterols, than the other supplement categories. Powders contained significantly higher (p < 0.05) concentrations of total fattyacids than tinctures, which contain negligible amounts of fattyacids (46.3 mg/g) and phytosterols (0.10 mg/g). Our findings suggest that liquid saw palmetto supplements may be the best choice for individuals who want to take a saw palmetto supplement with the highest concentrations of both fattyacids and phytosterols. PMID:24067389

The objective of our study was to extend the limited research available on the association between concentrations of milk fattyacids and elevated nonesterified fattyacids (NEFA) and β-hydroxybutyrate (BHB) concentrations in early lactation dairy cattle. Measurement of milk fattyacids for detection of cows in excessive negative energy balance has the potential to be incorporated in routine in-line monitoring systems. Blood samples were taken from 84 cows in second or greater lactation 3 times per week between 3 to 14 d in milk. Cows were characterized as hyperketonemic (HYK) if blood BHB concentration was ≥1.2mmol/L at least once and characterized as having elevated concentrations of NEFA (NEFAH) if serum NEFA concentration was ≥1mmol/L at least once. Composition of colostrum and milk fattyacids at wk 2 postpartum was used to investigate the potential diagnostic value of individual fattyacids and fattyacid ratios for the correct classification of cows with NEFA and BHB concentrations above these thresholds, respectively. Receiver operating characteristic (ROC) curves were used to identify thresholds of fattyacid concentration and fattyacid ratios when ROC area under the curve was ≥0.70. Correct classification rate (CCR, %) was calculated as {[(number of true positives + number of true negatives)/total number tested] × 100}. None of the colostrum fattyacids yielded a sufficiently high area under the curve in ROC analysis for the association with HYK and NEFAH. The following fattyacids and fattyacid ratios were identified for an association with NEFAH (threshold, CCR): C15:0 (≤0.65g/100g, 68.3%); cis-9 C16:1 (≥1.85g/100g, 70.7%); cis-9 C18:1 (≥26g/100g, 69.5%), cis-9 C18:1 to C15:0 ratio (≥45, 69.5%); cis-9 C16:1 to C15:0 (≥2.50, 73.2%). Several fattyacids were associated with HYK (threshold, CCR): C6:0 (≤1.68g/100g, 80.5%), C8:0 (≤0.80g/100g, 80.5%), C10:0 (≤1.6g/100g, 79.3%); C12:0 (≤1.42g/100g, 82.9%); C14:0 (≤6.10g/100g, 84

Considerable information has accumulated to show that DHA and EPA have unique roles that differ from other n-3 fattyacids and the n-6 fattyacids, with increasing understanding of the mechanisms through which these fattyacids reduce risk of disease. DHA and EPA regulate hepatic lipid and glucose metabolism, but are present in foods of animal origin, which are generally high in protein with variable triglycerides and low carbohydrate. Biological activity at intakes too low to provide significant amounts of energy is consistent with the definition of a vitamin for which needs are modified by life-stage, diet and genetic variables, and disease. Recent studies reveal that DHA may play a central role in co-coordinating complex networks that integrate hepatic glucose, fattyacid and amino acid metabolism for the purpose of efficient utilization of dietary protein, particularly during early development when the milk diet provides large amounts of energy from fat.

Electrophilic fattyacid nitroalkenes (NO(2)-FA) are products of nitric oxide and nitrite-mediated unsaturated fattyacid nitration. These electrophilic products induce pleiotropic signaling actions that modulate metabolic and inflammatory responses in cell and animal models. The metabolism of NO(2)-FA includes reduction of the vinyl nitro moiety by prostaglandin reductase-1, mitochondrial β-oxidation, and Michael addition with low molecular weight nucleophilic amino acids. Complex lipid reactions of fattyacid nitroalkenes are not well defined. Herein we report the detection and characterization of NO(2)-FA-containing triacylglycerides (NO(2)-FA-TAG) via mass spectrometry-based methods. In this regard, unsaturated fattyacids of dietary triacylglycerides are targets for nitration reactions during gastric acidification, where NO(2)-FA-TAG can be detected in rat plasma after oral administration of nitro-oleic acid (NO(2)-OA). Furthermore, the characterization and profiling of these species, including the generation of beta oxidation and dehydrogenation products, could be detected in NO(2)-OA-supplemented adipocytes. These data revealed that NO(2)-FA-TAG, formed by either the direct nitration of esterified unsaturated fattyacids or the incorporation of nitrated free fattyacids into triacylglycerides, contribute to the systemic distribution of these reactive electrophilic mediators and may serve as a depot for subsequent mobilization by lipases to in turn impact adipocyte homeostasis and tissue signaling events.

Electrophilic fattyacid nitroalkenes (NO2-FA) are products of nitric oxide and nitrite-mediated unsaturated fattyacid nitration. These electrophilic products induce pleiotropic signaling actions that modulate metabolic and inflammatory responses in cell and animal models. The metabolism of NO2-FA includes reduction of the vinyl nitro moiety by prostaglandin reductase-1, mitochondrial β–oxidation and Michael addition with low molecular weight nucleophilic amino acids. Complex lipid reactions of fattyacid nitroalkenes are not well defined. Herein we report the detection and characterization of NO2-FA-containing triacylglycerides (NO2-FA-TAG) via mass spectrometry-based methods. In this regard, unsaturated fattyacids of dietary triacylglycerides are targets for nitration reactions during gastric acidification, where NO2-FA-TAG can be detected in rat plasma after oral administration of nitro-oleic acid (NO2-OA). Furthermore, the characterization and profiling of these species, including the generation of beta oxidation and dehydrogenation products, could be detected in NO2-OA supplemented adipocytes. These data revealed that NO2-FA-TAG, formed by either the direct nitration of esterified unsaturated fattyacids or the incorporation of nitrated free fattyacids into triacylglycerides, contribute to the systemic distribution of these reactive electrophilic mediators and may serve as a depot for subsequent mobilization by lipases to in turn impact adipocyte homeostasis and tissue signaling events. PMID:26066303

Excess energy is stored primarily as triglycerides, which are mobilized when demand for energy arises. Dysfunction of energy balance by excess food intake leads to metabolic diseases, such as obesity and diabetes. Free fattyacids (FFAs) provided by dietary fat are not only important nutrients, but also contribute key physiological functions via FFA receptor (FFAR)-mediated signaling molecules, which depend on FFAs’ carbon chain length and the ligand specificity of the receptors. Functional analyses have revealed that FFARs are critical for metabolic functions, such as peptide hormone secretion and inflammation, and contribute to energy homeostasis. In particular, recent studies have shown that the administration of selective agonists of G protein-coupled receptor (GPR) 40 and GPR120 improved glucose metabolism and systemic metabolic disorders. Furthermore, the anti-inflammation and energy metabolism effects of short chain FAs have been linked to the activation of GPR41 and GPR43. In this review, we summarize recent progress in research on FFAs and their physiological roles in the regulation of energy metabolism. PMID:27023530

The contribution of dietary trans fattyacids (TFAs) on the risk of ischemic heart disease (IHD) has recently gained further support due to the results from large, prospective, population-based studies. Compared to saturated fat, TFAs are, gram to gram, associated with a considerably (2.5- to >10-fold) higher risk increment for IHD. A negative effect on the human fetus and on newborns and an increase in colon cancer risk in adults are possible but, however, still equivocal. Recent findings justify further studies concerning the effect of TFAs on allergic diseases in children and on the risk of type-2 diabetes in adults. The intake of industrially produced TFAs in European countries is decreasing. However, determination of the TFA content in various popular food items collected in Danish shops showed that it is likely that persons with a frequent intake of, e.g., French fries, microwave oven popcorn, chocolate bars, fast food, etc., consume industrially produced TFAs in amounts far exceeding the average intake, and are thereby exposed to an unnecessary health risk. The Danish government has decided that oils and fats containing more than 2% industrially produced TFAs will not be sold in Denmark after the January 1, 2004.

A proper balance between the n-3 and n-6 series of essential fattyacids (EFAs) is essential for homeostasis and normal growth in humans. Dietary supplement with fish oil and related n-3 EFAs has been used to study their antihypertensive property in animals and humans with borderline and essential hypertension. In the animal models, chronic treatment of young animals generally only attenuated the development of hypertension. In animals with hypercholesterolemia, n-3 EFA supplement increased the incidence of atherosclerosis. In humans, chronic treatment with fish oil only produced a small reduction in blood pressure. The concerns are that the high dose of fish oil may interfere with the control of blood glucose in diabetic patients, and may cause prolonged bleeding in surgical patients. Studies on the animal models of hypertension showed that n-6 EFAs are more effective than n-3 EFAs in lowering and normalizing the blood pressure of these animals, probably through the production of tissue prostaglandins, which favour vasodilation. The antihypertensive effect of the n-6 EFAs in humans is not well known, because there are only a few studies, usually involving a very small number of patients. A possible side effects of n-6 EFAs for concern is that they might stimulate tumour development. A careful examination of these risk factors is needed before any recommendation can be made concerning the use of EFAs for the control of hypertension for humans.

In the work, the in vitro antiproliferative activity of a series of synthetic fattyacid amides were investigated in seven cancer cell lines. The study revealed that most of the compounds showed antiproliferative activity against tested tumor cell lines, mainly on human glioma cells (U251) and human ovarian cancer cells with a multiple drug-resistant phenotype (NCI-ADR/RES). In addition, the fatty methyl benzylamide derived from ricinoleic acid (with the fattyacid obtained from castor oil, a renewable resource) showed a high selectivity with potent growth inhibition and cell death for the glioma cell line-the most aggressive CNS cancer.

Epoxygenated fattyacids (EpFAs), which are lipid mediators produced by cytochrome P450 epoxygenases from polyunsaturated fattyacids, are important signaling molecules known to regulate various biological processes including inflammation, pain and angiogenesis. The EpFAs are further metabolized by soluble epoxide hydrolase (sEH) to form fattyacid diols which are usually less-active. Pharmacological inhibitors of sEH that stabilize endogenous EpFAs are being considered for human clinical uses. Here we review the biology of ω-3 and ω-6 EpFAs on inflammation, pain, angiogenesis and tumorigenesis. PMID:24345640

In the stagnant loop syndrome an abnormal anaerobic flora colonizes the small bowel. Anaerobic organisms are characterized by fermentation reactions leading to the production of volatile fattyacids. This paper describes the measurement of intrajejunal volatile fattyacid concentrations in 11 patients with the stagnant loop syndrome. Nine normal persons and 18 patients with gastrointestinal disease without intestinal stasis acted as controls. Acetate and propionate concentrations were greatly increased in the patients with the stagnant loop syndrome and returned to normal in those patients treated with antibiotics. The measurement of intrajejunal volatile fattyacid concentrations as an index of overgrowth of anaerobic organisms is discussed.

One hundred and forty nine diabetic patients were ophthalmologically assessed seven years after randomisation to a low carbohydrate or modified fat diet (rich in linoleic acid). Glycaemic control, regardless of the type of diet, was a major determinant of the development of retinopathy. Poorly controlled patients (haemoglobin A1c greater than 8%) with low levels of linoleic acid in cholesterol ester had a significantly greater frequency of retinopathy than well controlled patients or patients with similarly unsatisfactory control but higher levels of linoleic acid. The findings support an earlier suggestion that linoleic acid might protect against diabetic retinopathy. PMID:3965024

The effect of dietary fattyacids on uterine fattyacid composition was studied in rats fed control diet or semi-synthetic diet supplemented with 1.5 microliter/g/day evening primrose oil (EPO) or fish oil (FO). Diet-related changes in uterine lipid were detected within 21 days. Changes of 2- to 20-fold were detected in the uterine n-6 and n-3 essential fattyacids (EFA) and in certain saturated and monounsaturated fattyacids. The FO diet was associated with higher uterine C20 and C22 n-3, and the EPO diet, with higher uterine n-6 fattyacid. High uterine C18:2 n-6 was detected in neutral lipid (NL) of rats fed high concentrations of this fattyacid, but there was little evidence of selective incorporation or retention of C18:2 n-6 by uterine NL. The incorporation of EFA into uterine phospholipids (PL) was greater than NL EFA incorporation, and uterine PL n-3/n-6 ratios showed greater diet dependence. Tissue/diet fattyacid ratios in NL and PL also indicated preferential incorporation/synthesis of C16:1 n-9, and C16:0, and there was greater incorporation of C12:0 and C14:0 into uteri of rats fed EPO and FO. Replacement of 50-60% of arachidonate with n-3 EFA in uterine PL may inhibit n-6 EFA metabolism necessary for uterine function at parturition.

Mobilization of fattyacids from adipose tissue during metabolic stress will increase the amount of free fattyacids in blood and follicular fluid and, thus, may affect oocyte quality. In this in vitro study, the three predominant fattyacids in follicular fluid (saturated palmitic and stearic acid and unsaturated oleic acid) were presented to maturing oocytes to test whether fattyacids can affect lipid storage of the oocyte and developmental competence postfertilization. Palmitic and stearic acid had a dose-dependent inhibitory effect on the amount of fat stored in lipid droplets and a concomitant detrimental effect on oocyte developmental competence. Oleic acid, in contrast, had the opposite effect, causing an increase of lipid storage in lipid droplets and an improvement of oocyte developmental competence. Remarkably, the adverse effects of palmitic and stearic acid could be counteracted by oleic acid. These results suggest that the ratio and amount of saturated and unsaturated fattyacid is relevant for lipid storage in the maturing oocyte and that this relates to the developmental competence of maturing oocytes.

This review outlines the molecular sensors that reprogram cellular metabolism in response to the ketogenic diet (KD). Special emphasis is placed on the fasting-, fattyacid- and drug-activated transcription factor, peroxisome proliferator-activated receptor alpha (PPARalpha). The KD causes a switch to ketogenesis that is coordinated with an array of changes in cellular lipid, amino acid, carbohydrate and inflammatory pathways. The role of both liver and brain PPARalpha in mediating such changes will be examined, with special reference to the anti-epileptic effects not only of the KD but a range of synthetic anti-epileptic drugs such as valproate. Finally, the implications of the KD and activated brain PPARalpha will be discussed in the context of their potential involvement in a range of disorders of neuro-degeneration and neuro-inflammation.

Adequate supply of LCPUFA from maternal plasma is crucial for fetal normal growth and development. The present study examines the effect of maternal micronutrients (folic acid and vitamin B12) and omega 3 fattyacids on placental mRNA levels of fattyacid desaturases (Δ5 and Δ6) and transport proteins. Pregnant female rats were divided into 6 groups at 2 levels of folic acid both in the presence and absence of vitamin B12. Both the vitamin B12 deficient groups were supplemented with omega 3 fattyacid. Maternal vitamin B12 deficiency reduced placental mRNA and protein levels of Δ5 desaturase, mRNA levels of FATP1 and FATP4 (p<0.05 for all) as compared to control while omega 3 fattyacid supplementation normalized the levels. Our data for the first time indicates that altered maternal micronutrients and omega 3 fattyacids play a key role in regulating fattyacid desaturase and transport protein expression in placenta.

Two experiments were carried out to determine whether ozone causes significant oxidation of pulmonary polyunsaturated fattyacids in vivo. These involved ad libitum and pair-feeding. In the first experiment, rats were fed fat-free diets and exposed to ozone for 0, 1, 2, and 4 weeks. Lung and liver fattyacids were analyzed to determine if the rats exposed to ozone lost essential fattyacids more rapidly than those exposed to filtered air. In the second experiment, rats were divided into four groups. Two of these groups were fed fat-free diets, and two were fed diets containing essential fattyacids. Rats from the two diet groups (one of each type) were exposed to ozone, while the remaining two groups were exposed to filtered air. In the second experiment, rats were pair-fed. The amounts of lung and liver fattyacids were relatively uninfluenced by breathing ozone. Results from these experiments demonstrate that in the lung, the polyunsaturated fattyacids, linoleic and arachidonic acids, appear to be oxidized by filtered air and ozone at essentially the same rate.

The ability of unsaturated fattyacid methyl esters to modify amino acid residues in bovine serum albumin (BSA), glutamine synthetase, and insulin in the presence of a metal-catalyzed oxidation system [ascorbate/Fe(III)/O2] depends on the degree of unsaturation of the fattyacid. The fattyacid-dependent generation of carbonyl groups and loss of lysine residues increased in the order methyl linoleate < methyl linolenate < methyl arachidonate. The amounts of alkyl hydroperoxides, malondialdehyde, and a number of other aldehydes that accumulated when polyunsaturated fattyacids were oxidized in the presence of BSA were significantly lower than that observed in the absence of BSA. Direct treatment of proteins with various lipid hydroperoxides led to a slight increase in the formation of protein carbonyl derivatives, whereas treatment with the hydroperoxides together with Fe(II) led to a substantial increase in the formation of protein carbonyls. These results are consistent with the proposition that metal-catalyzed oxidation of polyunsaturated fattyacids can contribute to the generation of protein carbonyls by direct interaction of lipid oxidation products (α,β-unsaturated aldehydes) with lysine residues (Michael addition reactions) and also by interactions with alkoxyl radicals obtained by Fe(II) cleavage of lipid hydroperoxides that are formed. In addition, saturated aldehydes derived from the polyunsaturated fattyacids likely react with lysine residues to form Schiff base adducts.

Many African diets are low in fat but are currently changing because of nutrition transition. We studied fat and fattyacid (FA) intake and the essential fattyacid (EFA) status of adolescent girls (aged 14-19 years, n 262) in Zambezia Province, central Mozambique. A cross-sectional study was carried out in a city as well as in the towns and rural villages of a coastal and an inland district. Dietary intake and FA sources were studied in a 24 h dietary recall. FA compositions of cholesteryl esters and phospholipids of non-fasting serum samples were analysed by GLC. Fat intake was low (13-18 % of energy) in all areas. Coconut and palm oil were the main sources of fat, and soyabean oil and maize were the main sources of PUFA. Compared to Food and Agriculture Organization/WHO 2010 recommendations, intake of linoleic acid (LA, 18 : 2n-6) was inadequate in the coastal district, and intakes of n-3 PUFA were inadequate in all areas. FA compositions of serum lipids differed between areas. The proportions of LA tended to be highest in the city and lowest in the rural areas. The phospholipid mead (20 : 3n-9):arachidonic acid (20 : 4n-6) ratio did not indicate EFA insufficiency. LA proportions in phospholipids were low, but those of long-chain n-6 and n-3 PUFA were high in comparison with Western adolescents. To conclude, fat sources, FA intake and EFA status differed between adolescent girls living in different types of communities. Fat intake was low, but EFA insufficiency was not indicated.

Fattyacids play important role in controlling oil quality of peanut. In addition to the major fattyacids, oleic acid (C18:1) and linoleic acid (C18:2) accounting for about 80%, there are several minor fattyacids accounting for about 20% in peanut oil, such as palmitic acid (PA, C16:0), stearic (S...

Twenty-nine specimens of calcareous sponges (Class Calcarea, Phylum Porifera), covering thirteen representative species of the families Soleneiscidae, Leucaltidae, Levinellidae, Leucettidae, Clathrinidae, Sycettidae, Grantiidae, Jenkinidae, and Heteropiidae were analysed for their fattyacids. The fattyacids of Calcarea generally comprise saturated and monounsaturated linear (n-), and terminally methylated (iso-, anteiso-) C(14)-C(20) homologues. Furthermore, polyunsaturated C(22) fattyacids and the isoprenoic 4,8,12-trimethyltridecanoic acid were found. The most prominent compounds are n-C(16), iso-C(17), iso-C(18), n-C(18), n-C(20). In addition, a high abundance of the exotic 16-methyloctadecanoic acid (anteiso-C(19)) appears to be a characteristic trait of Calcarea. Long-chain 'demospongic acids', typically found in Demospongiae and Hexactinellida, are absent in Calcarea. The completely different strategy of calcarean fattyacid synthesis supports their phylogenetic distinctiveness from a common Demospongiae/Hexactinellida taxon. Both intraspecific and intraclass patterns of Calcarea showed great similarity, suggesting a conserved fattyacid composition that already existed in the last common ancestor of Calcinea and Calcaronea, i.e. before subclasses diverged.

Omega-3 polyunsaturated fattyacids (PUFA) are essential unsaturated fattyacids with a double bond (C=C) starting after the third carbon atom from the end of the carbon chain. They are important nutrients but, unfortunately, mammals cannot synthesize them, whereby they must be obtained from food sources or from supplements. Amongst nutritionally important polyunsaturated n-3 fattyacids, α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are highly concentrated in the brain and have anti-oxidative stress, anti-inflammatory and antiapoptotic effects. They are involved in many bodily processes and may reportedly lead to neuron protection in neurological diseases. aged or damaged neurons and in Alzheimer's disease. Their effect in cognitive and behavioral functions and in several neurological and psychiatric disorders has been also proven. The dentate gyrus (DG), a sub-region of hippocampus, is implicated in cognition and mood regulation. The hippocampus represents one of the two areas in the mammalian brain in which adult neurogenesis occurs. This process is associated with beneficial effects on cognition, mood and chronic pharmacological treatment. The exposure to n-3 fattyacids enhances adult hippocampal neurogenesis associated with cognitive and behavioral processes, promotes synaptic plasticity by increasing long-term potentiation and modulates synaptic protein expression to stimulate the dendritic arborization and new spines formation. On this basis we review the effect of n-3 fattyacids on adult hippocampal neurogenesis and neuroplasticity. Moreover their possible use as a new therapeutic approach for neurodegenerative diseases is pointed out.

Ricinoleic acid (12-hydroxyoctadec-cis-9-enoic acid) has many specialized uses in bioproduct industries, while castor bean is currently the only commercial source for the fattyacid. This report describes metabolic engineering of a microbial system (Pichia pastoris) to produce ricinoleic acid using a "push" (synthesis) and "pull" (assembly) strategy. CpFAH, a fattyacid hydroxylase from Claviceps purpurea, was used for synthesis of ricinoleic acid, and CpDGAT1, a diacylglycerol acyl transferase for the triacylglycerol synthesis from the same species, was used for assembly of the fattyacid. Coexpression of CpFAH and CpDGAT1 produced higher lipid contents and ricinoleic acid levels than expression of CpFAH alone. Coexpression in a mutant haploid strain defective in the Δ12 desaturase activity resulted in a higher level of ricinoleic acid than that in the diploid strain. Intriguingly, the ricinoleic acid produced was mainly distributed in the neutral lipid fractions, particularly the free fattyacid form, but with little in the polar lipids. This work demonstrates the effectiveness of the metabolic engineering strategy and excellent capacity of the microbial system for production of ricinoleic acid as an alternative to plant sources for industrial uses.

Fattyacid metabolism has received significant attention as a route for producing high-energy density, liquid transportation fuels and high-value oleochemicals from renewable feedstocks. If microbes can be engineered to produce these compounds at yields that approach the theoretical limits of 0.3–0.4 g/g glucose, then processes can be developed to replace current petrochemical technologies. Here, we review recent metabolic engineering efforts to maximize production of free fattyacids (FFA) in Escherichia coli, the first step towards production of downstream products. To date, metabolic engineers have succeeded in achieving higher yields of FFA than any downstream products. Regulation of fattyacid metabolism and the physiological effects of fattyacid production will also be reviewed from the perspective of identifying future engineering targets. PMID:23102412

... conditions: (a) They are prepared from corn oil, cottonseed oil, lard, palm oil from fruit, peanut oil...) Polyglycerol esters of a mixture of stearic, oleic, and coconut fattyacids are used as a cloud inhibitor...

Patients with major depressive disorder have high rates of cardiovascular disease and other medical comorbidity. Omega-3 fattyacids, particularly those found in fish and seafood, have cardiovascular health benefits and may play an adjunctive role in the treatment of mood disorders. However, existing studies on omega-3 fattyacids in depression have limitations such as small sample sizes and a wide variance in study design, and results regarding efficacy are mixed. The preponderance of data from placebo-controlled treatment studies suggests that omega-3 fattyacids are a reasonable augmentation strategy for the treatment of major depressive disorder. More research is necessary before omega-3 supplements can be recommended as monotherapy for the treatment of depression. For many individuals with major depressive disorder, augmentation with omega-3 fattyacids should be considered, as general health benefits are well established and adjunctive use is low risk.

Microalgae are a promising feedstock for biodiesel and other liquid fuels due to their fast growth rate, high lipid yields, and ability to grow in a broad range of environments. However, many microalgae achieve maximal lipid yields only under stress conditions hindering growth and providing compositions not ideal for biofuel applications. Metabolic engineering of algal fattyacid biosynthesis promises to create strains capable of economically producing fungible and sustainable biofuels. The algal fattyacid biosynthetic pathway has been deduced by homology to bacterial and plant systems, and much of our understanding is gleaned from basic studies in these systems. However, successful engineering of lipid metabolism in algae will necessitate a thorough characterization of the algal fattyacid synthase (FAS) including protein-protein interactions and regulation. This review describes recent efforts to engineer fattyacid biosynthesis toward optimizing microalgae as a biodiesel feedstock.

The MYB family of transcription factors is important in regulatory networks controlling development, metabolism and responses to biotic and abiotic stresses in Arabidopsis. However, their role in regulating fattyacid accumulation in seeds is still largely unclear. Here, we found that MYB76, localized in the nucleus, was predominantly expressed in developing seeds during maturation. The myb76 mutation caused a significant increase in the amounts of total fattyacids and several major fattyacid compositions in mature seeds, suggesting that MYB76 functioned as an important repressor during seed oil biosynthesis. RNA sequencing and quantitative real-time PCR analysis revealed remarkable alteration of numerous genes involved in photosynthesis, fattyacid biosynthesis, modification, and degradation, and oil body formation in myb76 seeds at 12 days after pollination. These results help us to understand the novel function of MYB76 and provide new insights into the regulatory network of MYB transcriptional factors controlling seed oil accumulation in Arabidopsis. PMID:28270825

A comparative study between two methods (lipid extraction followed by saponification and methylation, and direct methylation) to determine the fattyacids in egg yolk was evaluated. Direct methylation of the samples resulted in lower fattyacid content and greater variation in the results than the lipid extraction followed by saponification and methylation. The low repeatability observed for the direct HCl methylation method was probably due to a less efficient extraction and conversion of the fattyacids into their methyl esters as compared to the same procedure starting with the lipid extract. As the lipid extraction followed by esterification method was shown to be more precise it was validated using powdered egg certified as reference material (RM 8415, NIST) and applied to samples of egg, egg enriched with polyunsaturated omega-3 fattyacids (n-3 PUFA), and commercial spray-dried whole egg powder.

Not only short chain ω-hydroxycarboxylic acids, α,ω-dicarboxylic acids, and ω-aminocarboxylic acids but also medium to long chain carboxylic acids are widely used as building blocks and intermediates in the chemical, pharmaceutical, and food industries. Thereby, recent achievements in biological production of medium to long chain carboxylic acids are addressed here. ω-Hydroxycarboxylic and α,ω-dicarboxylic acids were synthesized via terminal CH bond oxygenation of fattyacids and/or internal oxidative cleavage of the fattyacid carbon skeletons. ω-Aminocarboxylic acids were enzymatically produced from ω-hydroxycarboxylic acids via ω-oxocarboxylic acids. Productivities and product yields of some of the products are getting close to the industrial requirements for large scale production.

Very high gravity (VHG) fermentation is the mainstream technology in ethanol industry, which requires the strains be resistant to multiple stresses such as high glucose concentration, high ethanol concentration, high temperature and harsh acidic conditions. To our knowledge, it was not reported previously that any ethanol-producing microbe showed a high performance in VHG fermentations without amino acid and vitamin. Here we demonstrate the engineering of a xylose utilizing recombinant Zymomonas mobilis for VHG ethanol fermentations. The recombinant strain can produce ethanol up to 136 g/L without amino acid and vitamin with a theoretical yield of 90 %, which is significantly superior to that produced by all the reported ethanol-producing strains. The intracellular fattyacids of the bacterial were about 16 % of the bacterial dry biomass, with the ratio of ethanol:fattyacids was about 273:1 (g/g). The recombinant strain was achieved by a multivariate-modular strategy tackles with the multiple stresses which are closely linked to the ethanol productivity of Z. mobilis. The over-expression of metB/yfdZ operon enabled the growth of the recombinant Z. mobilis in a chemically defined medium without amino acid and vitamin; and the fattyacids overproduction significantly increased ethanol tolerance and ethanol production. The coupled production of ethanol with fattyacids of the Z. mobilis without amino acid and vitamin under VHG fermentation conditions may permit a significant reduction of the production cost of ethanol and microbial fattyacids.

Developing Brassica napus embryos are primarily concerned with the accumulation of storage products, namely oil, starch and protein. The presence of fattyacid catabolic pathways in the background of this biosynthetic activity was investigated. Enzymes involved in the process of lipid mobilization, such as malate synthase and isocitrate lyase, are detectable towards the late stages of embryo development. [(14)C]Acetate feeding experiments also reveal that fattyacid catabolism becomes increasingly functional as the embryo matures.

Medium-chain fattyacids (MCFAs, 4-12 carbons) are valuable as precursors to industrial chemicals and biofuels, but are not canonical products of microbial fattyacid synthesis. We engineered microbial production of the full range of even-and odd-chain-length MCFAs and found that MCFA production is limited by rapid, irreversible elongation of their acyl-ACP precursors. To address this limitation, we programmed an essential ketoacyl synthase to degrade in response to a chemical inducer, thereby slowing acyl-ACP elongation and redirecting flux from phospholipid synthesis to MCFA production. Our results show that induced protein degradation can be used to dynamically alter metabolic flux, and thereby increase the yield of a desired compound. The strategy reported herein should be widely useful in a range of metabolic engineering applications in which essential enzymes divert flux away from a desired product, as well as in the production of polyketides, bioplastics, and other recursively synthesized hydrocarbons for which chain-length control is desired.

An earlier study showed that essential fattyacids and their metabolites can kill tumor cells in vitro. This tumoricidal action can be correlated to an increase in generation of free radicals in the tumor cells. Evening primrose oil (EPO) is a rich source of linoleic acid and gamma-linolenic acid. We report that EPO can kill tumor cells both in vitro and in vivo. This tumoricidal action of EPO was associated with a threefold increase in superoxide generation. One of the factors that is capable of interfering with the cytotoxic action of fattyacids appears to be the protein content of the medium. Fattyacids can bind to protein and thus prevent their cytotoxic action.

A method of recovering crude oil for subsequent processing. The method contemplates the step of exposing the source of crude oil such as a subterranean petroleum reservoir or a vessel or container of tar sands, kerogen or the like to aliphatic or carboxylic acid, preferably oleic acid, to produce a solvated crude oil mixture of reduced viscosity. This mixture is saponifyed by reacting it with a nucleophilic base, preferably a hydroxide of potassium or sodium, under pressure whereby to separate the solvated mixture into petroleum crude and an acid soap which migrates to an aqueous phase. The petroleum crude is separated from the aqueous soap through conventional techniques. Afterwards, a desaponification step contemplates recovery of the aliphatic or carboxylic acid for subsequent recycling in the previously mentioned exposing step. Reuse is facilitated by desaponifying aqueous soap within a high pressure containment vessel reacted with an acid suitable for donating a hydrated proton to the aqueous phase of the soap. This reconstituted acid is recycled for injection into the inputting step. Preferably carbonic acid is generated for the desaponifying step by injecting high pressure carbon dioxide within the containment vessel. By-products of the chemical reaction are separated and/or filtered as necessary to effectuate necessary purification sub-steps.

During stress or senescence, thylakoid membranes in chloroplasts are disintegrated, and chlorophyll and galactolipid are broken down, resulting in the accumulation of toxic intermediates, i.e., tetrapyrroles, free phytol, and free fattyacids. Chlorophyll degradation has been studied in detail, but the catabolic pathways for phytol and fattyacids remain unclear. A large proportion of phytol and fattyacids is converted into fattyacid phytyl esters and triacylglycerol during stress or senescence in chloroplasts. We isolated two genes (PHYTYL ESTER SYNTHASE1 [PES1] and PES2) of the esterase/lipase/thioesterase family of acyltransferases from Arabidopsis thaliana that are involved in fattyacid phytyl ester synthesis in chloroplasts. The two proteins are highly expressed during senescence and nitrogen deprivation. Heterologous expression in yeast revealed that PES1 and PES2 have phytyl ester synthesis and diacylglycerol acyltransferase activities. The enzymes show broad substrate specificities and can employ acyl-CoAs, acyl carrier proteins, and galactolipids as acyl donors. Double mutant plants (pes1 pes2) grow normally but show reduced phytyl ester and triacylglycerol accumulation. These results demonstrate that PES1 and PES2 are involved in the deposition of free phytol and free fattyacids in the form of phytyl esters in chloroplasts, a process involved in maintaining the integrity of the photosynthetic membrane during abiotic stress and senescence.

Mammalian fattyacid synthase is a classic example of a chain-building multienzyme. A cornerstone of its mechanism has been the obligatory collaboration of two identical subunits, with fatty acyl intermediates transferring between them. Now, fresh evidence has upset this view.

Labile aggregation stimulating substance (LASS), an intermediate produced during platelet biosynthesis of PGE2 and PGF2alpha, acts as a physiologic intercellular messenger to promote platelet aggregation and the release reaction. The activity is formed by intact cells after physiologic stimulation or can be generated from platelet membrane fractions after combination with arachidonate. In the present investigation, small amounts of polyunsaturated fattyacids added to an incubation mixture of platelet microsomes and arachidonate were found to significantly inhibit subsequent platelet aggregation. Saturated and mono-unsaturated fattyacids in the same concentrations were without effect. However, in higher concentrations mono-unsaturated fattyacids were found to be inhibitory and stearic acid was found to enhance subsequent platelet aggregation. The inhibition caused by the polyunsaturated fattyacid, linoleate, was shown to be the result of an effect on the production of LASS through an interaction with the platelet enzyme responsible for conversion of arachidonate to LASS. In contrast, stearic acid was found to enhance platelet aggregation by acting on the platelets and not directly on LASS production. The results suggest that small changes in the fattyacid composition of platelet phospholipids could significantly influence platelet reactivity.

Ascaris suum eggs were inactivated in distilled water and digested sludge by butanoic, pentanoic and hexanoic acids. The fattyacids (FA) were only effective when protonated and at sufficient concentration. The conjugate bases were not effective at the concentrations evaluated. Predictions from an ...

Gas-liquid chromatography was used to study the effects of saponification/methylation and thin-layer chromatographic isolation on the analyses of polyunsaturated fattyacids. Using selected procedures, the qualitative and quantitative distribution of these acids in marine organisms can be determined with a high degree of accuracy. ?? 1977 Springer-Verlag.

The idea of renewable and regenerative resources has inspired research for more than a hundred years. Ideally, the only spent energy will replenish itself, like plant material, sunlight, thermal energy or wind. Biodiesel or ethanol are examples, since their production relies mainly on plant material. However, it has become apparent that crop derived biofuels will not be sufficient to satisfy future energy demands. Thus, especially in the last decade a lot of research has focused on the production of next generation biofuels. A major subject of these investigations has been the microbial fattyacid biosynthesis with the aim to produce fattyacids or derivatives for substitution of diesel. As an industrially important organism and with the best studied microbial fattyacid biosynthesis, Escherichia coli has been chosen as producer in many of these studies and several reviews have been published in the fields of E. coli fattyacid biosynthesis or biofuels. However, most reviews discuss only one of these topics in detail, despite the fact, that a profound understanding of the involved enzymes and their regulation is necessary for efficient genetic engineering of the entire pathway. The first part of this review aims at summarizing the knowledge about fattyacid biosynthesis of E. coli and its regulation, and it provides the connection towards the production of fattyacids and related biofuels. The second part gives an overview about the achievements by genetic engineering of the fattyacid biosynthesis towards the production of next generation biofuels. Finally, the actual importance and potential of fattyacid-based biofuels will be discussed. PMID:24405789

Nutritional status of Lake Michigan Chinook salmon (Oncorhynchus tshawytscha) is inadequately documented. An investigation was conducted to determine muscle and liver thiamine content and whole body fattyacid composition in small, medium and large Chinook salmon. Muscle and liver thiamine concentrations were highest in small salmon, and tended to decrease with increasing fish size. Muscle thiamine was higher in fall than spring in large salmon. The high percentage of Chinook salmon (24-32% in fall and 58-71% in spring) with muscle thiamine concentration below 500 pmol/g, which has been associated with loss of equilibrium and death in other Great Lake salmonines, suggest that Chinook appear to rely less on thiamine than other Great Lakes species for which such low concentrations would be associated with thiamine deficiency (Brown et al. 2005b). A positive correlation was observed between liver total thiamine and percent liver lipids (r = 0.53, P < 0.0001, n = 119). In medium and large salmon, liver lipids were observed to be low in fish with less than 4,000 pmol/g liver total thiamine. In individuals with greater than 4,000 pmol/g liver thiamine, liver lipid increased with thiamine concentration. Individual fattyacids declined between fall and spring. Essential omega-3 fattyacids appear to be conserved as lipid content declined. Arachidonic acid (C20:4n6), an essential omega-6 fattyacid was not different between fall and spring, although the sum of omega-6 (Sw6) fattyacids declined over winter. Elevated concentrations of saturated fattyacids (sum) were observed in whole body tissue lipid. In summary, thiamine, a dietary essential vitamin, and individual fattyacids were found to vary in Lake Michigan Chinook salmon by fish size and season of the year.

The blood-brain barrier (BBB), formed by the brain capillary endothelial cells, provides a protective barrier between the systemic blood and the extracellular environment of the CNS. Passage of fattyacids from the blood to the brain may occur either by diffusion or by proteins that facilitate their transport. Currently several protein families have been implicated in fattyacid transport. The focus of the present study was to identify the fattyacid transport proteins (FATPs) expressed in the brain microvessel endothelial cells and characterize their involvement in fattyacid transport across an in vitro BBB model. The major fattyacid transport proteins expressed in human brain microvessel endothelial cells (HBMEC), mouse capillaries and human grey matter were FATP-1, -4 and fattyacid binding protein 5 and fattyacid translocase/CD36. The passage of various radiolabeled fattyacids across confluent HBMEC monolayers was examined over a 30-min period in the presence of fattyacid free albumin in a 1 : 1 molar ratio. The apical to basolateral permeability of radiolabeled fattyacids was dependent upon both saturation and chain length of the fattyacid. Knockdown of various fattyacid transport proteins using siRNA significantly decreased radiolabeled fattyacid transport across the HBMEC monolayer. Our findings indicate that FATP-1 and FATP-4 are the predominant fattyacid transport proteins expressed in the BBB based on human and mouse expression studies. While transport studies in HBMEC monolayers support their involvement in fattyacid permeability, fattyacid translocase/CD36 also appears to play a prominent role in transport of fattyacids across HBMEC.

L1210 leukemia cells can utilize all of the main fattyacids that normally are present in the ascites fluid in which they grow. This finding is consistent with the view that L1210 cells derive most of their fattyacids from the ascites fluid. From 80--90% of each fattyacid was incorporated into cell lipids without structural modification, suggesting that the lipid composition of these cells can be altered by changing the type of fattyacids to which they are exposed. Most importantly, the palmitate that was subsequently incorporated into total cell phospholipids was elongated and desaturated somewhat more than that incorporated into triglycerides. This difference was due primarily to more extensive modification of the palmitate incorporated into the ethanolamine phosphoglycerides fraction. Although there was no difference between total phospholipids and triglycerides with linoleate, more of the linoleate incorporated into ethanolamine phosphoglycerides was elongated and further desaturated than that incorporated into choline phosphoglycerides and triglycerides. These findings indicate fattyacids incorporated into various cell lipid fractions are not structurally modified to the same extent. There appears to be greater modification of fattyacid used for ethanolamine phosphoglyceride synthesis as compared with triglyceride and choline phosphoglyceride synthesis.

The separation of fatty and resinic acidic fractions from crude tall-oil soap solutions with n-heptane by the technique of dissociation extraction is discussed. The theory of the overall process is supported by a systematic study developed to cover the high selectivity demonstrated in the differential solubility and the aptness between fatty and diterpenic acids to both liquids phases. To study the main factors affecting those liquid-liquid extraction systems and the amphiphilic behavior of such molecules involved, sodium salts aqueous solutions of crude tall oil and synthetic mixtures as molecular acidic models were used.

Fattyacids, in addition to its known energy value and its structural function, have other beneficial properties. In particular, the polyunsaturated fattyacids omega-3 acting on the cardiovascular apparatus through many channels exerting a protective effect against cardiovascular risk. The benefits associated with the reduction in cardiac mortality and sudden death particular, are related to the incorporation of EPA and DHA in phospholipid membrane of cardiomyocytes. An index is established that relates the percentage of EPA + DHA of total fattyacids in erythrocytes and risk of death from cardiovascular disease may layering in different degrees. Therefore, the primary source of fatty fish w-3 PUFA, behaves like a reference food in cardiosaludables diets.

The mammalian brain and central nervous system are especially dependent on the omega-3 (n-3) fattyacid docosahexaenoic acid (DHA) for normative signaling and function, and research suggests that n-3 fattyacid deficiencies are one contributing factor in the increasing prevalence of depressive disorders. However, the reasons for which n-3 fattyacids and mood are connected remain unknown. Atrophy in the hippocampus is one of the most significant neuroanatomical findings in depressed patients, and current therapies for depression tend to increase hippocampal neurogenesis. We recently discovered that the fat-1 transgenic mouse, which has enriched levels of DHA in the brain because it can convert n-6 to n-3 fattyacids, exhibits increased hippocampal neurogenesis. This finding suggests a mechanism by which omega-3 could influence depression and mood; here we expand on the argument that n-3 fattyacids, and DHA in particular, may help prevent and treat depression by virtue of their effects on neurogenesis in the hippocampus. Because DHA can be obtained through the diet, increasing DHA intake in depressed patients or those at risk for depression may be one way of managing the disease and perhaps providing aid to those who have not been able to achieve remission via pharmacological means.

Omega-3/('-3) or n-3 fattyacids are a family of unsaturated fattyacids that have in common a final carbon-carbon double bond in the n-3 position. n-3 Fattyacids which are important in human nutrition are: a-linolenic acid (18:3, n-3; ALA), eicosapentaenoic acid (20:5, n-3; EPA), and docosahexaen...

Conversion of biomass feedstock to chemicals and fuels has attracted increasing attention recently. Soybean meal, containing significant quantities of carbohydrates, is an inexpensive renewable feedstock. Glucose, galactose, and fructose can be obtained by enzymatic hydrolysis of soluble carbohydrates of soybean meal. Free fattyacids (FFAs) are valuable molecules that can be used as precursors for the production of fuels and other value-added chemicals. In this study, free fattyacids were produced by mutant Escherichia coli strains with plasmid pXZ18Z (carrying acyl-ACP thioesterase (TE) and (3R)-hydroxyacyl-ACP dehydratase) using individual sugars, sugar mixtures, and enzymatic hydrolyzed soybean meal extract. For individual sugar fermentations, strain ML211 (MG1655 fadD(-) fabR(-) )/pXZ18Z showed the best performance, which produced 4.22, 3.79, 3.49 g/L free fattyacids on glucose, fructose, and galactose, respectively. While the strain ML211/pXZ18Z performed the best with individual sugars, however, for sugar mixture fermentation, the triple mutant strain XZK211 (MG1655 fadD(-) fabR(-) ptsG(-) )/pXZ18Z with an additional deletion of ptsG encoding the glucose-specific transporter, functioned the best due to relieved catabolite repression. This strain produced approximately 3.18 g/L of fattyacids with a yield of 0.22 g fattyacids/g total sugar. Maximum free fattyacids production of 2.78 g/L with a high yield of 0.21 g/g was achieved using soybean meal extract hydrolysate. The results suggested that soybean meal carbohydrates after enzymatic treatment could serve as an inexpensive feedstock for the efficient production of free fattyacids.

In our previously study, we reported lower tear volume in with an n-3 fattyacid deficient mice and that the docosahexaenoic acid and total n-3 fattyacid levels in these mice are significantly reduced in the meibomian gland, which secretes an oily tear product. Furthermore, we noted very long chain fattyacids (≥25 carbons) in the meibomian gland. To verify the detailed mechanism of the low tear volume in the n-3 fattyacid-deficient mice, we identified the very long chain fattyacids in the meibomian gland, measured the fattyacid composition in the tear product. Very long chain fattyacids were found to exist as monoesters. In particular, very long chain fattyacids with 25-29 carbons existed for the most part as iso or anteiso branched-chain fattyacids. n-3 fattyacid deficiency was decreased the amount of meibum secretion from meibomian gland without change of fattyacid composition. These results suggest that the n-3 fattyacid deficiency causes the enhancement of evaporation of tear film by reducing oily tear secretion along with the decrease of meibomian gland function.

The cellular fattyacid compositions were determined for 42 strains of Pseudomonas cepacia from five cystic fibrosis centers in North America. All isolates contained significant (20%) amounts of hexadecanoic (C16:0), and cis-9 hexadecenoic (C16:1 cis9) acids and an isomer of octadecenoic acid (C18:1). None had hydroxy acids containing fewer than 14 carbon atoms. The quantitative data from the fattyacid analysis were highly reproducible and provided a basis for numerical analysis. Five subgroups comprising all the strains were obtained by cluster analysis and further characterized by principal-component analysis. With minor exceptions, the predominant subgroup identified in each center was different from that identified in other centers and accounted for one-half of the isolates within each center. Cellular fattyacid composition is a useful adjunct to biochemical characterization for the identification of P. cepacia isolated from cystic fibrosis patients. Numerical analysis of the fattyacid data can separate P. cepacia into subgroups, which may provide useful epidemiologic information or a basis for further analysis by more complex techniques such as DNA probe analysis. PMID:2687315

2-Alkynoic fattyacids display antimycobacterial, antifungal, and pesticidal activities but their antiprotozoal activity has received little attention. In this work we synthesized the 2-octadecynoic acid (2-ODA), 2-hexadecynoic acid (2-HDA), and 2-tetradecynoic acid (2-TDA) and show that 2-ODA is the best inhibitor of the Leishmania donovani DNA topoisomerase IB enzyme (LdTopIB) with an EC(50)=5.3±0.7μM. The potency of LdTopIB inhibition follows the trend 2-ODA>2-HDA>2-TDA, indicating that the effectiveness of inhibition depends on the fattyacid carbon chain length. All of the studied 2-alkynoic fattyacids were less potent inhibitors of the human topoisomerase IB enzyme (hTopIB) as compared to LdTopIB. 2-ODA also displayed in vitro activity against Leishmania donovani (IC(50)=11.0μM), but it was less effective against other protozoa, Trypanosoma cruzi (IC(50)=48.1μM) and Trypanosoma brucei rhodesiense (IC(50)=64.5μM). The antiprotozoal activity of the 2-alkynoic fattyacids, in general, followed the trend 2-ODA>2-HDA>2-TDA. The experimental information gathered so far indicates that 2-ODA is a promising antileishmanial compound.

The integrity of gastric barrier derives from the balance between defending and damaging factors. In particular, prostaglandins play a relevant role in the maintenance of gastric homeostasis and prevention of peptic disease, at different levels. Omega-3 fattyacids, particularly eicosapentanoic acid, are the precursors of the third series of prostaglandins (with anti-inflammatory properties), also reducing the formation of the second series of prostaglandins (pro-inflammatory ones). Such a pathophysiological rationale brought to the experimental application, both in animal models and, more recently, in humans, of omega-3 fattyacids against gastrointestinal damage. Omega-3 fattyacids have shown interesting results in preventing different types of gastric damage in mouse models. A large retrospective case-control study on patients taking both anti-thrombotic therapy and eicosapentanoic acid showed (although only at unadjusted analysis) an inverse correlation between consumption of eicosapentanoic acid and gastrointestinal injury. Prospective, well-designed, comparative studies are warranted to clarify if omega-3 fattyacids may represent, or not, a novel resort against gastrointestinal injury.

Among the fattyacids, it is the omega-3 polyunsaturated fattyacids (PUFA) which possess the most potent immunomodulatory activities, and among the omega-3 PUFA, those from fish oil-eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)--are more biologically potent than alpha-linolenic acid (ALA). Some of the effects of omega-3 PUFA are brought about by modulation of the amount and types of eicosanoids made, and other effects are elicited by eicosanoid-independent mechanisms, including actions upon intracellular signaling pathways, transcription factor activity and gene expression. Animal experiments and clinical intervention studies indicate that omega-3 fattyacids have anti-inflammatory properties and, therefore, might be useful in the management of inflammatory and autoimmune diseases. Coronary heart disease, major depression, aging and cancer are characterized by an increased level of interleukin 1 (IL-1), a proinflammatory cytokine. Similarly, arthritis, Crohn's disease, ulcerative colitis and lupus erythematosis are autoimmune diseases characterized by a high level of IL-1 and the proinflammatory leukotriene LTB(4) produced by omega-6 fattyacids. There have been a number of clinical trials assessing the benefits of dietary supplementation with fish oils in several inflammatory and autoimmune diseases in humans, including rheumatoid arthritis, Crohn's disease, ulcerative colitis, psoriasis, lupus erythematosus, multiple sclerosis and migraine headaches. Many of the placebo-controlled trials of fish oil in chronic inflammatory diseases reveal significant benefit, including decreased disease activity and a lowered use of anti-inflammatory drugs.

Genetic modification is useful for improving the nutritional qualities of cyanobacteria. To increase the total unsaturated fattyacid content, along with the ratio of ω-3/ω-6 fattyacids, genetic engineering can be used to modify fattyacid metabolism. Synechococcus sp. PCC7002, a fast-growing cyanobacterium, does not contain a Δ6 desaturase gene and is therefore unable to synthesize γ-linolenic acid (GLA) and stearidonic acid (SDA), which are important in human health. In this work, we constructed recombinant vectors Syd6D, Syd15D and Syd6Dd15D to express the Δ15 desaturase and Δ6 desaturase genes from Synechocystis PCC6803 in Synechococcus sp. PCC7002, with the aim of expressing polyunsaturated fattyacids. Overexpression of the Δ15 desaturase gene in Synechococcus resulted in 5.4 times greater accumulation of α-linolenic acid compared with the wild-type while Δ6 desaturase gene expression produced both GLA and SDA. Co-expression of the two genes resulted in low-level accumulation of GLA but much larger amounts of SDA, accounting for as much to 11.64% of the total fattyacid content.

Feeding experiments and laboratory analyses were conducted to establish the essential fattyacid (EFA) requirement of red drum (Sciaenops ocellatus). Juvenile red drum were maintained in aquaria containing brackish water (5 ± 2‰ total dissolved solids) for two 6-week experiments. Semipurified diets contained a total of 70% lipid consisting of different combinations of tristearin [predominantly 18:0] and the following fattyacid ethyl esters: oleate, linoleate, linolenate, and a mixture of highly unsaturated fattyacids (HUFA) containing approximately 60% eicosapentaenoate plus docosahexaenoate. EFA-deficient diets (containing only tristearin or oleate) rapidly reduced fish growth and feed efficiency, and increased mortality. Fin erosion and a "shock syndrome" also occurred in association with EFA deficiency. Of the diets containing fattyacid ethyl esters, those with 0.5-1% (n-3) HUFA (0.3-0.6% eicosapentaenoate plus docosahexaenoate) promoted the best growth, survival, and feed efficiency; however, the control diet containing 7% menhaden fish oil provided the best performance. Excess (n-3) HUFA suppressed fish weight gain; suppression became evident at 1.5% (n-3) HUFA, and was pronounced at 2.5%. Fattyacid compositions of whole-body, muscle and liver tissues from red drum fed the various diets generally reflected dietary fattyacids, but modifications of these patterns also were evident. Levels of saturated fattyacids appeared to be regulated independent of diet. In fish fed EFA-deficient diets (containing only tristearin or oleate), monoenes increased and (n-3) HUFA were preferentially conserved in polar lipid fractions. Eicosatrienoic acid [20:3(n-9)] was not elevated in EFA-deficient red drum, apparently due to their limited ability to transform fattyacids. Red drum exhibited some limited ability to elongate and desaturate linoleic acid [18:2(n-6)] and linolenic acid [18:3(n-3)]; however, metabolism of 18:3(n-3) did not generally result in increased

The ability to allocate resources, even when limited, is essential for survival and fitness. We examine how nutrients that occur in minute amounts are allocated among reproductive, somatic, and metabolic demands. In addition to sugar, flower nectars contain two macronutrients-amino acids and fattyacids. We created artificial nectars spiked with (13)C-labelled amino acids and fattyacids and fed these to adult moths (Manduca sexta: Sphingidae) to understand how they allocate these nutrients among competing sinks (reproduction, somatic tissue, and metabolic fuel). We found that both essential and non-essential amino acids were allocated to eggs and flight muscles and were still detectable in early-instar larvae. Parental-derived essential amino acids were more conserved in the early-instars than non-essential amino acids. All amino acids were used as metabolic fuel, but the non-essential amino acids were oxidized at higher rates than essential amino acids. Surprisingly, the nectar fattyacids were not vertically transferred to offspring, but were readily used as a metabolic fuel by the moth, minimizing losses of endogenous nutrient stores. We conclude that the non-carbohydrate components of nectar may play important roles in both reproductive success and survival of these nectar-feeding animals.

Increasing the production of fattyacids by microbial fermentation remains an important step towards the generation of biodiesel and other portable liquid fuels. In this work, we report an Escherichia coli strain engineered to overexpress a fragment consisting of four dehydratase domains from the polyunsaturated fattyacid (PUFA) synthase enzyme complex from the deep-sea bacterium, Photobacterium profundum. The DH1-DH2-UMA enzyme fragment was excised from its natural context within a multi-enzyme PKS and expressed as a stand-alone protein. Fattyacids were extracted from the cell pellet, esterified with methanol and quantified by GC-MS analysis. Results show that the E. coli strain expressing the DH tetradomain fragment was capable of producing up to a 5-fold increase (80.31 mg total FA/L culture) in total fattyacids over the negative control strain lacking the recombinant enzyme. The enhancement in production was observed across the board for all the fattyacids that are typically made by E. coli. The overexpression of the DH tetradomain did not affect E. coli cell growth, thus showing that the observed enhancement in fattyacid production was not a result of effects associated with cell density. The observed enhancement was more pronounced at lower temperatures (3.8-fold at 16 °C, 3.5-fold at 22 °C and 1.5-fold at 30 °C) and supplementation of the media with 0.4% glycerol did not result in an increase in fattyacid production. All these results taken together suggest that either the dehydration of fattyacid intermediates are a limiting step in the E. coli fattyacid biosynthesis machinery, or that the recombinant dehydratase domains used in this study are also capable of catalyzing thioester hydrolysis of the final products. The enzyme in this report is a new tool which could be incorporated into other existing strategies aimed at improving fattyacid production in bacterial fermentations towards accessible biodiesel precursors. PMID:24411456

Increasing the production of fattyacids by microbial fermentation remains an important step toward the generation of biodiesel and other portable liquid fuels. In this work, we report an Escherichia coli strain engineered to overexpress a fragment consisting of four dehydratase domains from the polyunsaturated fattyacid (PUFA) synthase enzyme complex from the deep-sea bacterium, Photobacterium profundum. The DH1-DH2-UMA enzyme fragment was excised from its natural context within a multi-enzyme PKS and expressed as a stand-alone protein. Fattyacids were extracted from the cell pellet, esterified with methanol and quantified by GC-MS analysis. Results show that the E. coli strain expressing the DH tetradomain fragment was capable of producing up to a 5-fold increase (80.31 mg total FA/L culture) in total fattyacids over the negative control strain lacking the recombinant enzyme. The enhancement in production was observed across the board for all the fattyacids that are typically made by E. coli. The overexpression of the DH tetradomain did not affect E. coli cell growth, thus showing that the observed enhancement in fattyacid production was not a result of effects associated with cell density. The observed enhancement was more pronounced at lower temperatures (3.8-fold at 16 °C, 3.5-fold at 22 °C and 1.5-fold at 30 °C) and supplementation of the media with 0.4% glycerol did not result in an increase in fattyacid production. All these results taken together suggest that either the dehydration of fattyacid intermediates are a limiting step in the E. coli fattyacid biosynthesis machinery, or that the recombinant dehydratase domains used in this study are also capable of catalyzing thioester hydrolysis of the final products. The enzyme in this report is a new tool which could be incorporated into other existing strategies aimed at improving fattyacid production in bacterial fermentations toward accessible biodiesel precursors.

During lipolysis, adipose tissue triacylglycerols (TAG) undergo concurrent breakdown and synthesis because some of the newly hydrolysed and released non-esterified ('free') fattyacids (NEFA) can subsequently be taken up and re-esterified. The present study examines whether and how the release of individual fattyacids is affected by the re-uptake of some of the newly hydrolysed fattyacids in vitro during lipolysis. To alter fattyacid release and re-uptake, adipose tissue fragments and isolated adipocytes from rats were incubated under various conditions, i.e. several cell concentrations or adipose fragment quantities, with or without glucose. In the various conditions tested, the NEFA/glycerol molar ratio ranged from 1.5 to 2.9. Whatever the incubation conditions, including those resulting in very low, medium or high fattyacid re-uptake (as assessed by the NEFA/glycerol ratio), the percentage weight of fattyacids in NEFA was significantly different from that in TAG for 20-24 of the 35 fattyacids that were considered. Thus the greater the fattyacid re-uptake, the higher the proportion of polyunsaturated fattyacids and the lower the proportion of long-chain saturated and monounsaturated fattyacids in NEFA. Moreover, the relative mobilization (%NEFA/%TAG) of the least readily mobilized fattyacid (C(22:1,n-11)) was 6.2-fold lower than that of the most readily mobilized fattyacid (C(20:5,n-3)) under conditions of very low fattyacid re-uptake, and 14.8-fold lower under conditions of high fattyacid re-uptake, indicating a widening of the range of relative mobilizations. We conclude that the composition of the NEFA pool is affected by the rate of fattyacid re-uptake. This provides strong evidence for the selective re-uptake of adipose tissue fattyacids during lipolysis. PMID:10794723

The fattyacid compositions of the hyperthermophilic microorganisms Thermotoga maritima and Pyrococcus furiosus were studied and compared. A total of 37 different fattyacids were identified in T. maritima, including the novel 13,14-dimethyloctacosanedioic acid. In contrast, a total of 18 different fattyacids were characterized, as minor components, in P. furiosus, and these included saturated, monounsaturated, and dicarboxylic acids. This is the first report of fattyacids from an archaeon. PMID:9098079

The objective of this study is to investigate the effects of high pressure processing on the molecular structure of some unsaturated fattyacids. Samples of elaidic acid, linoleic acid, ZE and EE conjugated linoleic acid are treated at 293 or 333 K at pressures up to 700 MPa. It is observed that the adiabatic heat generated from compression is able to bring the sample temperature above 373 K after 700 MPa. These relatively extreme conditions are of great interest for food sterilization, but they may induce undesirable change in fattyacid quality characteristics. To check for structural changes, Raman spectra of the samples are analysed after treatments. The comparison with Raman spectra of samples kept at atmospheric pressure shows that pressure induces some conformational changes at the hydrocarbon skeleton in solid samples, while the liquid ones remain unchanged. No cis/trans isomerization occurs, but gauche conformers are likely to be present.

The present invention relates to methods for producing fattyacid desaturase mutants having a substantially increased activity towards substrates with fewer than 18 carbon atom chains relative to an unmutagenized precursor desaturase having an 18 carbon chain length specificity, the sequences encoding the desaturases and to the desaturases that are produced by the methods. The present invention further relates to a method for altering a function of a protein, including a fattyacid desaturase, through directed mutagenesis involving identifying candidate amino acid residues, producing a library of mutants of the protein by simultaneously randomizing all amino acid candidates, and selecting for mutants which exhibit the desired alteration of function. Candidate amino acids are identified by a combination of methods. Enzymatic, binding, structural and other functions of proteins can be altered by the method.

Microalgae are important primary producers in the marine ecosystem and excellent sources of lipids and other bioactive compounds. The marine diatom Phaeodactylum tricornutum accumulates eicosapentaenoic acid (EPA, 20:5n-3) as its major component of fattyacids. To improve the EPA production, delta 5 desaturase, which plays a role in EPA biosynthetic pathway, was characterized in P. tricornutum. An annotated delta 5 desaturase PtD5b gene was cloned and overexpressed in P. tricornutum. The transgene was integrated into the genome demonstrated by Southern blot, and the overexpression of PtD5b was verified by qPCR and Western blot analysis. Fattyacid composition exhibited a significant increase in the unsaturated fattyacids. Monounsaturated fattyacids (MUFA) and polyunsaturated fattyacids (PUFA) showed an increase of 75% and 64%, respectively. In particular, EPA showed an increase of 58% in engineered microalgae. Meanwhile, neutral lipid content showed an increase up to 65% in engineered microalgae. More importantly, engineered cells showed a similar growth rate with the wild type, thus keeping high biomass productivity. This work provides an effective way to improve the production of microalgal value-added bioproducts by metabolic engineering.

Although ethanol causes acute pancreatitis (AP) and lipolytic fattyacid (FA) generation worsens AP, the contribution of ethanol metabolites of FAs, ie, FA ethyl esters (FAEEs), to AP outcomes is unclear. Previously, pancreata of dying alcoholics and pancreatic necrosis in severe AP, respectively, showed high FAEEs and FAs, with oleic acid (OA) and its ethyl esters being the most abundant. We thus compared the toxicities of FAEEs and their parent FAs in severe AP. Pancreatic acini and peripheral blood mononuclear cells were exposed to FAs or FAEEs in vitro. The triglyceride of OA (i.e., glyceryl tri-oleate) or OAEE was injected into the pancreatic ducts of rats, and local and systemic severities were studied. Unsaturated FAs at equimolar concentrations to FAEEs induced a larger increase in cytosolic calcium, mitochondrial depolarization, and necro-apoptotic cell death. Glyceryl tri-oleate but not OAEE resulted in 70% mortality with increased serum OA, a severe inflammatory response, worse pancreatic necrosis, and multisystem organ failure. Our data show that FAs are more likely to worsen AP than FAEEs. Our observations correlate well with the high pancreatic FAEE concentrations in alcoholics without pancreatitis and high FA concentrations in pancreatic necrosis. Thus, conversion of FAs to FAEE may ameliorate AP in alcoholics. PMID:26878214

We present case histories of two young children with episodes of hypoglycemia, elevation of SGOT, low insulin levels, increased urinary excretion of psi-hydroxy fattyacids (5-hydroxyhexanoic, 7-hydroxyoctanoic and 9-hydroxydecanoic), traces of the corresponding psi-ketoacids and elevations of urinary adipic, suberic, and sebacic acids. The ratio of psi-hydroxy fattyacids to 3-hydroxybutyric in the urine of these patients is higher than in patients of similar ages with similar illnesses. These acids persisted while the patients were well. Increased urinary psi-hydroxy fattyacids could be reproduced by a load of medium chain triglycerides without precipitating other clinical symptoms. Three children with hypoglycemia were found not to excrete measurable amounts of these unusual acids while ill. A medium chain triglyceride load in one of these children after recovery failed to elicit psi-hydroxy acid excretion. Small amounts of urinary 5-hydroxyhexanoic acid only were found in two patients with acute Reye's syndrome and in three of five severely ill children with starvation ketonuria. In this last group, no urinary psi-hydroxyacids could be detected after recovery. Normal children do not excrete measurable amounts (less than 1 mg/g creatinine) of these psi-hydroxyacids.

Iron-enriched smectites play an important role in adsorption and transformation of soil organic components. Soil organo-clay complexes, and in particular humin contain hydroxy fattyacids, which are derived from plant biopolymer cutin. Phenolic acids belong to another major group of organic acids detected in soil. They participate in various soil processes, and are of concern due to their allelopathic activity. We studied the reactivity of iron-enriched smectites (Fe(III)-montmorillonite and nontronite) toward both groups of acids. We used fattyacids- 9(10),16-dihydroxypalmitic acid (diHPA), isolated from curtin, and 9,10,16-trihydroxypalmitic acid (triHPA); the following phenolic acids were used: ferulic, p-coumaric, syringic, and vanillic. Adsorption of both groups of acids was measured. The FTIR spectra of fattyacid-mineral complexes indicated inner-sphere complexation of fattyacids with iron-enriched smectites (versus outer-sphere complexation with Ca(II)-montmorillonite). The LC-MS results demonstrated enhanced esterification of fattyacids on the iron-enriched smectite surfaces (as compared to Ca(II)-montmorillonite). This study suggests that fattyacids can be esterified on the iron-enriched smectite surfaces, which results in the formation of stable organo-mineral complexes. These complexes may serve as a model for the study of natural soil organo-clay complexes and humin. The reaction of phenolic acids with Fe(III)-montmorillonite demonstrated their oxidative transformation by the mineral surfaces, which was affected by molecular structure of acids. The following order of their transformation was obtained: ferulic >syringic >p-coumaric >vanillic. The LC-MS analysis demonstrated the presence of dimers, trimers, and tetramers of ferulic acid on the surface of Fe(III)-montmorillonite. Oxidation and transformation of ferulic acid were more intense on the surface of Fe(III)-montmorillonite as compared to Fe(III) in solution due to stronger complexation on

Ricinoleate, a monohydroxy fattyacid in castor oil, has many industrial uses. Dihydroxy and trihydroxy fattyacids can also be used in industry. We report here the identification of diacylglycerols and triacylglycerols containing trihydroxy fattyacids in castor oil. The Ci8 HPLC fractions of casto...

A series of batch cultures were conducted to investigate the effects of oleic acid (OA) on in vitro ruminal dry matter degradability (IVDMD), gas production, methane (CH4) and hydrogen (H2) production, and proportion of fattyacids. Rumen fluid was collected from fistulated goats, diluted with incubation buffer, and then incubated with 500 mg Leymus chinensis meal supplemented with different amounts of OA (0, 20, 40, and 60 mg for the CON, OA20, OA40 and OA60 groups, respectively). Incubation was carried out anaerobically at 39°C for 48 h, and the samples were taken at 12, 24 and 48 h and subjected to laboratory analysis. Supplementation of OA decreased IVDMD, the cumulative gas production, theoretical maximum of gas production and CH4 production, but increased H2 production. However, no effect was observed on any parameters of rumen fermentation (pH, ammonia, production of acetate, propionate and butyrate and total volatile fattyacid production). The concentrations of some beneficial fattyacids, such as cis monounsaturated fattyacids and conjugated linoleic acid (CLA) were higher (P < 0.05) from OA groups than those from the control group at 12 h incubation. In summary, these results suggest that the OA supplementation in diet can reduce methane production and increase the amount of some beneficial fattyacids in vitro. PMID:27299526

Skeletal muscle is a plastic tissue capable of adapting and mal-adapting to physical activity and diet. The response of skeletal muscle to adaptive stimuli, such as exercise, can be modified by the prior nutritional status of the muscle. The influence of nutrition on skeletal muscle has the potential to substantially impact physical function and whole body metabolism. Animal and cell based models show that omega-3 fattyacids, in particular those of marine origin, can influence skeletal muscle metabolism. Furthermore, recent human studies demonstrate that omega-3 fattyacids of marine origin can influence the exercise and nutritional response of skeletal muscle. These studies show that the prior omega-3 status influences not only the metabolic response of muscle to nutrition, but also the functional response to a period of exercise training. Omega-3 fattyacids of marine origin therefore have the potential to alter the trajectory of a number of human diseases including the physical decline associated with aging. We explore the potential molecular mechanisms by which omega-3 fattyacids may act in skeletal muscle, considering the n-3/n-6 ratio, inflammation and lipidomic remodelling as possible mechanisms of action. Finally, we suggest some avenues for further research to clarify how omega-3 fattyacids may be exerting their biological action in skeletal muscle.

Limiting the saturated fattyacid (SAFA) consumption forms the basis of dietary fat recommendations for heart health, despite several meta-analyses demonstrating no link between dietary SAFA and the risk of cardiovascular disease (CVD). Three experts on dietary fat and health discussed the evidence of reducing SAFA intake at a symposium of the Federation of European Nutrition Societies in Berlin, Germany, October 23, 2015. Ronald P. Mensink, Maastricht University, the Netherlands, discussed the evidence linking dietary fattyacids and CVD risk. He emphasized the importance of the replacement nutrient(s) when SAFA intake is reduced. Julie Lovegrove, University of Reading, UK, addressed the question of whether higher intakes of unsaturated fattyacids are beneficial. She discussed the replacement of SAFA by polyunsaturated fattyacids (PUFA) and monounsaturated fattyacids (MUFA), noting the reduction in CVD risk with PUFA replacement and in CVD risk markers with MUFA replacement of SAFA. Ursula Schwab, University of Eastern Finland, Kuopio, Finland, discussed the importance of dietary patterns in achieving reduced risk of CVD, observing that several dietary patterns following the principles of a health-promoting diet and adapted to local customs, food preferences and seasonality are effective in reducing the risk of CVD, type 2 diabetes and other chronic diseases. This paper summarizes the symposium presentations.

The evidence for the cardioprotective nature of omega-3 fattyacids is abundant, and currently available data indicate that patients with known coronary heart disease should consume at least 1 g daily of long-chain omega-3 fattyacids from either oily fish or fish-oil supplements, and that individuals without disease should consume at least 250-500 mg daily. However, this area of research poses two questions. Firstly, which is the best source of omega-3 fattyacids-fish or fish-oil supplements? Secondly, are recommendations for omega-3 supplementation warranted in view of the rapid depletion of world fish stocks? The argument that eating fish is better than taking fish-oil supplements stems from the fact that several important nutrients, such as vitamin D, selenium, and antioxidants, are missing from the supplements. However, three major prevention trials have clearly indicated that omega-3 fattyacid capsules confer cardiovascular benefits and, therefore, that both are cardioprotective. Sustainable sources of omega-3 fattyacids will need to be identified if long-term cardiovascular risk reduction is to be achieved at the population level.

The aims of the present study were to evaluate essential fattyacids (EFA) and long-chain PUFA (LCPUFA) status in lactating adolescents and its association with breast milk composition. Healthy nursing adolescents from Rio de Janeiro, Brazil (n 30; 14-19 years; 30-120 d postpartum), exclusively or predominantly breast-feeding, participated in this study. Breast milk and blood samples were collected after overnight fasting. Fattyacid composition of breast milk, erythrocyte membrane (EM) and plasma NEFA were determined by GC. Indices of fattyacid status (mean melting point (MMP); EFA status index; DHA status indices, 22 : 5n-6:22 : 4n-6 and 22 : 6n-3:22 : 5n-6 ratios) were calculated from EM fattyacid composition. Dietary intake of n-3 fattyacids was low when compared with current recommendations for lactating women. MMP was associated with indices of DHA status, some individual fattyacids in EM and years post-menarche and weeks postpartum, suggesting the use of erythrocyte MMP as a possible comprehensive biochemical marker of LCPUFA status in this physiological condition. The DHA status of lactating adolescents and their milk DHA concentrations were similar to the values of Brazilian lactating adults, but lower compared with the values of lactating adults from other countries. Therefore, these lactating adolescents were apparently not disadvantaged, as compared with the Brazilian adults, when EM and breast milk fattyacid composition were considered. In general, PUFA in milk from adolescents presented few associations with their concentrations in plasma NEFA and with maternal status. However, milk DHA was associated with maternal LCPUFA and DHA states.

Several sources of long-chain polyunsaturated fattyacids (LCP) have been evaluated for infant-formula supplementation. These sources differ in their chemical structure [triglyceride (TG) or phospholipid (PL)], arrangement of fattyacids on the TG or PL backbone, fattyacid composition and presence of other lipid components. All of these characteristics influence fat digestion, may affect fat and fattyacid absorption, and hence, LCP bioavailability and metabolism in infancy. The main objective of this work was to establish the influence of different dietary LCP sources on overall fat and LCP absorption in early life. We compared fat and fattyacid excretions at weaning in rats fed control diets or diets supplemented with LCP as TG or PL. Two separate experiments were conducted. In Experiment 1, weanling rats were fed for 3 wk a control diet (C1), a diet with TG from tuna and fungal oils (TF-TG) or a diet with PL from pig brain concentrate (PB-PL). In Experiment 2, weanling rats were fed for 3 wk a control diet (C2), a diet containing egg-TG (EG-TG) or a diet containing egg-PL (EG-PL). Fat, mineral and saturated fattyacid excretions in feces were higher in rats fed PB-PL compared with those fed TF-TG diet. In Experiment 2, groups did not differ in fat and mineral excretions. However, the EG-PL group had lower fecal excretions of saturated fattyacids than the C2 and EG-TG groups. The 16:1(n-7), 18:1(n-9), 18:2(n-6) and 22:6(n-3) levels in feces were higher in the EG-TG group than in the EG-PL group. In summary, total fat and LCP excretions differed among rats fed diets supplemented with LCP from different sources.

A disturbed fattyacid metabolism increases the risk of adult non-communicable diseases. This study examines the effect of maternal micronutrients on the fattyacid composition, desaturase activity, mRNA levels of fattyacid desaturases and transport proteins in the liver. Pregnant female rats were divided into 6 groups at 2 levels of folic acid both in the presence and absence of vitamin B(12). The vitamin B(12) deficient groups were supplemented with omega 3 fattyacid. An imbalance of maternal micronutrients reduces liver docosahexaenoic acid, increases Δ5 desaturase activity but decreases mRNA levels, decreases Δ6 desaturase activity but not mRNA levels as compared to control. mRNA level of Δ5 desaturase reverts back to the levels of the control group as a result of omega 3 fattyacid supplementation. Our data for the first time indicates that maternal micronutrients differentially alter the activity and expression of fattyacid desaturases in the liver.

Five major fattyacids, palmitic (16:0), stearic (18:0), oleic (18:1), linoleic (18:2), and linolenic (18:3), were identified in polar lipid extracts from pulvini of Samanea saman and Phaseolus coccineus. In P. coccineus their distribution varied quantitatively in the laminar pulvinus, petiolar pulvinus, petiole, stem, leaf and root. Short pulses of red light did not greatly affect the relative quantities of fattyacids in dark grown P. coccineus, but a 30-minute exposure of red light generally increased the degree of unsaturation by increasing linolenic acid and decreasing linoleic and palmitic acids. P. coccineus seeds were exposed to several substituted pyridazinones as well as cerulenin and dimethylethanolamine. The pyridazinones San 6706 and norflurazon altered fattyacid composition but also altered morphology and inhibited chlorophyll synthesis. Exposure to 10 C for 72 hours caused a small but significant increase in the degree of unsaturation of P. coccineus fattyacids but results were equivocal with S. saman. PMID:16660990

Fattyacid amino acid conjugates (FACs) are known elicitors of induced release of volatile compounds in plants that, in turn, attract foraging parasitoids. Since the discovery of volicitin [N-(17-hydroxylinolenoyl)-L-glutamine] in the regurgitant of larval Spodoptera exigua1, a series of related FAC...

Since the first fattyacid amino acid conjugate (FAC) was isolated from regurgitant of Spodoptera exigua larvae in 1997 [volicitin: N-(17-hydroxylinolenoyl)- L-glutamine], their role as elicitors of induced responses in plants has been well documented. However, studies of the biosyntheses as well as...

Fattyacid amino acid conjugates (FACs) in regurgitant of larval Spodoptera exigua1 were initially identified as plant volatile elicitors and research has been focused on this apparent ecological disadvantage rather than on possible benefit for the caterpillar itself. Recently, we demonstrated that...

Oleic acid and oleic acid rich foods may have beneficial health effects in humans. Soybeans with high oleic acid (around 80% in seed oil) have been developed. Soybean sprouts are an important vegetable in Korea, Japan and China. The objective of this study was to investigate the variation of unsaturated fattyacids, oleic, linoleic and α-linolenic acids, in sprouts from soybeans with normal and high oleic acid concentration. Twelve soybean accessions with six high oleic acid lines, three parents of high oleic acid lines, and three checks with normal and high oleic acid concentration were used in this study. The unsaturated fattyacid concentration in sprouts from each genotype was similar to the concentration in the ungerminated seed. The oleic acid concentration in the sprouts of high oleic acid lines (up to 80%) was still high (>70%) compared to the ungerminated seed. Thus, high oleic soybean varieties developed for sprout production could add valuable health benefits to sprouts and the individuals who consume this vegetable.

Microbial production of fattyacids and fatty alcohols has attracted increasing concerns because of energy crisis and environmental impact of fossil fuels. Therefore, simple and efficient methods for the extraction and quantification of these compounds become necessary. In this study, a high-performance liquid chromatography-refractive index detection (HPLC-RID) method was developed for the simultaneous quantification of fattyacids and fatty alcohols in these samples. The optimum chromatographic conditions are C18 column eluted with methanol:water:acetic acid (90:9.9:0.1, v/v/v); column temperature, 26°C; flow rate, 1.0mL/min. Calibration curves of all selected analytes showed good linearity (r(2)≥0.9989). The intra-day and inter-day relative standard deviations (RSDs) of the 10 compounds were less than 4.46% and 5.38%, respectively, which indicated that the method had good repeatability and precision. Besides, a method for simultaneous extraction of fattyacids and fatty alcohols from fermentation broth was optimized by orthogonal design. The optimal extraction conditions were as follows: solvent, ethyl acetate; solvent to sample ratio, 0.5:1; rotation speed, 2min at 260rpm; extraction temperature, 10°C. This study provides simple and fast methods to simultaneously extract and quantify fattyacids and fatty alcohols for the first time. It will be useful for the study of microbial production of these products.

Coconut oil, the main product of coconut fruit, is the richest source of glycerol and lauric acid and hence is called lauric oil. This paper reports the fattyacid profile of oil from 60 Talls, 14 Dwarfs, and 34 hybrids. These include collections from 13 countries covering a large coconut-growing area of the world, apart from the indigenous ones. Capillary gas chromatography analysis of oil indicated a wider variation for the fattyacid profile than earlier reported. Apart from this, for the first time other fattyacids such as behenic and lignoceric acids were detected. Oil from cultivars and hybrids of coconut has significantly differed, particularly for commercially important fattyacids such as lauric acid and unsaturated fattyacids. However, coconut oil seems to have a conserved fattyacid profile, mainly because of low unsaturated fattyacids, indicating the possibility of grouping cultivars on the basis of their fattyacid profiles. The cluster analysis based on fattyacid profile indicated grouping together of geographically and typically closely related cultivars. Cultivars with high concentrations of specific fattyacids can be of potential use for industrial exploitation, whereas those with high concentrations of short- and medium-chain fattyacids and unsaturated fattyacids are more suitable for human consumption. Cultivars and hybrids with high and low values for each of the fattyacids are also identified.

The conversion of the plant-derived omega-3 (n-3) α-linolenic acid (ALA, 18:3n-3) to the long-chain eicosapentaenoic acid (EPA, 20:5n-3) and docosahexaenoic acid (DHA, 22:6n-3) can be increased by ALA sufficient diets compared to ALA deficient diets. Diets containing ALA above an optimal level result in no further increase in DHA levels in animals and humans. The present study evaluates means of maximizing plasma DHA accumulation by systematically varying both linoleic acid (LA, 18:2n-6) and ALA dietary level. Weanling rats were fed one of 54 diets for three weeks. The diets varied in the percentage of energy (en%) of LA (0.07-17.1 en%) and ALA (0.02-12.1 en%) by manipulating both the fat content and the balance of vegetable oils. The peak of plasma phospholipid DHA (>8% total fattyacids) was attained as a result of feeding a narrow dietary range of 1-3 en% ALA and 1-2 en% LA but was suppressed to basal levels (∼2% total fattyacids) at dietary intakes of total polyunsaturated fattyacids (PUFA) above 3 en%. We conclude it is possible to enhance the DHA status of rats fed diets containing ALA as the only source of n-3 fattyacids but only when the level of dietary PUFA is low (<3 en%).

Cyclopropane fattyacids (CPA) have been found in certain gymnosperms, Malvales, Litchi and other Sapindales. The presence of their unique strained ring structures confers physical and chemical properties characteristic of unsaturated fattyacids with the oxidative stability displayed by saturated fattyacids making them of considerable industrial interest. While cyclopropenoid fattyacids (CPE) are well-known inhibitors of fattyacid desaturation in animals, CPE can also inhibit the stearoyl-CoA desaturase and interfere with the maturation and reproduction of some insect species suggesting that in addition to their traditional role as storage lipids, CPE can contribute to the protection of plants from herbivory. Three genes encoding cyclopropane synthase homologues GhCPS1, GhCPS2 and GhCPS3 were identified in cotton. Determination of gene transcript abundance revealed differences among the expression of GhCPS1, 2 and 3 showing high, intermediate and low levels, respectively, of transcripts in roots and stems; whereas GhCPS1 and 2 are both expressed at low levels in seeds. Analyses of fattyacid composition in different tissues indicate that the expression patterns of GhCPS1 and 2 correlate with cyclic fattyacid (CFA) distribution. Deletion of the N-terminal oxidase domain lowered GhCPS's ability to produce cyclopropane fattyacid by approximately 70%. GhCPS1 and 2, but not 3 resulted in the production of cyclopropane fattyacids upon heterologous expression in yeast, tobacco BY2 cell and Arabidopsis seed. In cotton GhCPS1 and 2 gene expression correlates with the total CFA content in roots, stems and seeds. That GhCPS1 and 2 are expressed at a similar level in seed suggests both of them can be considered potential targets for gene silencing to reduce undesirable seed CPE accumulation. Because GhCPS1 is more active in yeast than the published Sterculia CPS and shows similar activity when expressed in model plant systems, it represents a strong candidate gene for

Women with evidence of high intake ratios of the marine omega-3 fattyacids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) relative to the omega-6 arachidonic acid have been found to have a reduced risk of breast cancer compared with those with low ratios in some but not all case-control and cohort studies. If increasing EPA and DHA relative to arachidonic acid is effective in reducing breast cancer risk, likely mechanisms include reduction in proinflammatory lipid derivatives, inhibition of nuclear factor-κB-induced cytokine production, and decreased growth factor receptor signaling as a result of alteration in membrane lipid rafts. Primary prevention trials with either risk biomarkers or cancer incidence as endpoints are underway but final results of these trials are currently unavailable. EPA and DHA supplementation is also being explored in an effort to help prevent or alleviate common problems after a breast cancer diagnosis, including cardiac and cognitive dysfunction and chemotherapy-induced peripheral neuropathy. The insulin-sensitizing and anabolic properties of EPA and DHA also suggest supplementation studies to determine whether these omega-3 fattyacids might reduce chemotherapy-associated loss of muscle mass and weight gain. We will briefly review relevant omega-3 fattyacid metabolism, and early investigations in breast cancer prevention and survivorship.

The bolus intravenous injection of a novel medium-chain triglyceride:fish oil emulsion to normal subjects was recently reported to enrich within 60 min the phospholipid content of leucocytes and platelets in long-chain polyunsaturated omega3 fattyacids. The present study, conducted in second generation omega3-depleted rats, aims at investigating whether such a procedure may also increase within 60 min the phospholipid content of omega3 fattyacids in cells located outwards of the bloodstream, in this case liver cells, and whether this coincides with correction of the perturbation in the liver triglyceride fattyacid content and profile otherwise prevailing in these rats. The results indicate that such is indeed the case and further suggest a cause-to-effect relationship between the two events.

Nitroalkene fattyacid derivatives manifest a strong electrophilic nature, are clinically detectable, and induce multiple transcriptionally regulated anti-inflammatory responses. At present, the characterization and quantification of endogenous electrophilic lipids are compromised by their Michael addition with protein and small-molecule nucleophilic targets. Herein, we report a trans-nitroalkylation reaction of nitro-fattyacids with beta-mercaptoethanol (BME) and apply this reaction to the unbiased identification and quantification of reaction with nucleophilic targets. Trans-nitroalkylation yields are maximal at pH 7 to 8 and occur with physiological concentrations of target nucleophiles. This reaction is also amenable to sensitive mass spectrometry-based quantification of electrophilic fattyacid-protein adducts upon electrophoretic resolution of proteins. In-gel trans-nitroalkylation reactions also permit the identification of protein targets without the bias and lack of sensitivity of current proteomic approaches. Using this approach, it was observed that fattyacid nitroalkenes are rapidly metabolized in vivo by a nitroalkene reductase activity and mitochondrial beta-oxidation, yielding a variety of electrophilic and nonelectrophilic products that could be structurally characterized upon BME-based trans-nitroalkylation reaction. This strategy was applied to the detection and quantification of fattyacid nitration in mitochondria in response to oxidative inflammatory conditions induced by myocardial ischemia-reoxygenation.

Background Methylmercury, a worldwide contaminant of fish and seafood, can cause adverse effects on the developing nervous system. However, long-chain n-3 polyunsaturated fattyacids in seafood provide beneficial effects on brain development. Negative confounding will likely result in underestimation of both mercury toxicity and nutrient benefits unless mutual adjustment is included in the analysis. Methods We examined these associations in 176 Faroese children, in whom prenatal methylmercury exposure was assessed from mercury concentrations in cord blood and maternal hair. The relative concentrations of fattyacids were determined in cord serum phospholipids. Neuropsychological performance in verbal, motor, attention, spatial, and memory functions was assessed at 7 years of age. Multiple regression and structural equation models (SEMs) were carried out to determine the confounder-adjusted associations with methylmercury exposure. Results A short delay recall (in percent change) in the California Verbal Learning Test (CVLT) was associated with a doubling of cord blood methylmercury (−18.9, 95% confidence interval [CI] = −36.3, −1.51). The association became stronger after the inclusion of fattyacid concentrations in the analysis (−22.0, 95% confidence interval [CI] = −39.4, −4.62). In structural equation models, poorer memory function (corresponding to a lower score in the learning trials and short delay recall in CVLT) was associated with a doubling of prenatal exposure to methylmercury after the inclusion of fattyacid concentrations in the analysis (−1.94, 95% CI = −3.39, −0.49). Conclusions Associations between prenatal exposure to methylmercury and neurobehavioral deficits in memory function at school age were strengthened after fattyacid adjustment, thus suggesting that n-3 fattyacids need to be included in analysis of similar studies to avoid underestimation of the associations with methylmercury exposure. PMID:24561639

The single gene encoding cyclopropane fattyacid synthetase (CFAS) is present in Leishmania infantum, L. mexicana and L. braziliensis but absent from L. major, a causative agent of cutaneous leishmaniasis. In L. infantum, usually causative agent of visceral leishmaniasis, the CFAS gene is transcribed in both insect (extracellular) and host (intracellular) stages of the parasite life cycle. Tagged CFAS protein is stably detected in intracellular L. infantum but only during the early log phase of extracellular growth, when it shows partial localisation to the endoplasmic reticulum. Lipid analyses of L. infantum wild type, CFAS null and complemented parasites detect a low abundance CFAS-dependent C19Δ fattyacid, characteristic of a cyclopropanated species, in wild type and add-back cells. Sub-cellular fractionation studies locate the C19Δ fattyacid to both ER and plasma membrane-enriched fractions. This fattyacid is not detectable in wild type L. major, although expression of the L. infantum CFAS gene in L. major generates cyclopropanated fattyacids, indicating that the substrate for this modification is present in L. major, despite the absence of the modifying enzyme. Loss of the L. infantum CFAS gene does not affect extracellular parasite growth, phagocytosis or early survival in macrophages. However, while endocytosis is also unaffected in the extracellular CFAS nulls, membrane transporter activity is defective and the null parasites are more resistant to oxidative stress. Following infection in vivo, L. infantum CFAS nulls exhibit lower parasite burdens in both the liver and spleen of susceptible hosts but it has not been possible to complement this phenotype, suggesting that loss of C19Δ fattyacid may lead to irreversible changes in cell physiology that cannot be rescued by re-expression. Aberrant cyclopropanation in L. major decreases parasite virulence but does not influence parasite tissue tropism. PMID:23251490

For each omega halogenated fattyacid there exists a potential omega hydroxy fattyacid and the corresponding macrocyclic lactone. The authors have utilized such lactones as starting materials for omega /sup 123/I fattyacid analogs intended for myocardial imaging. Macrocyclic musk lactones are industrially available; 120 analogs are described in the literature. The preparation requires saponification, tosylation, and radio-iodide substitution. Iodo-fattyacids are readily separated from tosylate fattyacids on TLC. While providing a secure source of 16-iodo-hexadecanoic acid and 17-iodo-heptadecanoic acid, the scheme allows ready access to a large number of untried fattyacid analogs. Examples presented are 16-iodo-hexadecanoic acid, 16-iodo-7-hexadecanoic acid, 16-iodo-12-oxa-hexadecanoic acid, 15-iodo-pentadecanoic acid, and 15-iodo-12-keto-pentadecanoic acid. Metabolic studies are in progress in mice and dogs to assess the utility of these analogs for myocardial imaging.

This paper reviews the factors affecting the fattyacid composition of adipose tissue and muscle in pigs, sheep and cattle and shows that a major factor is the total amount of fat. The effects of fattyacid composition on meat quality are also reviewed. Pigs have high levels of polyunsaturated fattyacids (PUFA), including the long chain (C20-22) PUFA in adipose tissue and muscle. The full range of PUFA are also found in sheep adipose tissue and muscle whereas cattle 'conserve' long chain PUFA in muscle phospholipid. Linoleic acid (18:2n-6) is a major ingredient of feeds for all species. Its incorporation into adipose tissue and muscle in relation to the amount in the diet is greater than for other fattyacids. It is deposited in muscle phospholipid at a high level where it and its long chain products eg aracidonic acid (20:4n-6) compete well for insertion into phospholipid molecules. Its proportion in pig adipose tissue declines as fat deposition proceeds and is an index of fatness. The same inverse relationships are not seen in ruminant adipose tissue but in all species the proportion of 18:2n-6 declines in muscle as fat deposition increases. The main reason is that phospholipid, where 18:2n-6 is located, declines as a proportion of muscle lipid and the proportion of neutral lipid, with its higher content of saturated and monounsaturated fattyacids, increases. Oleic acid (18:1cis-9), formed from stearic acid (18:0) by the enzyme stearoyl Co-A desaturase, is a major component of neutral lipid and in ruminants the same enzyme forms conjugated linoleic acid (CLA), an important nutrient in human nutrition. Like 18:2n-6, α-linolenic acid (18:3n-3) is an essential fattyacid and is important to ruminants since it is the major fattyacid in grass. However it does not compete well for insertion into phospholipid compared with 18:2n-6 and its incorporation into adipose tissue and muscle is less efficient. Greater biohydrogenation of 18:3n-3 and a long rumen transit time

The effects of postharvest oxalic acid (OA) treatment on chilling injury, energy metabolism and membrane fattyacid content in 'Baifeng' peach fruit stored at 0°C were investigated. Internal browning was significantly reduced by OA treatment in peaches. OA treatment markedly inhibited the increase of ion leakage and the accumulation of malondialdehyde. Meanwhile, OA significantly increased the contents of adenosine triphosphate and energy charge in peach fruit. Enzyme activities of energy metabolism including H(+)-adenosine triphosphatase, Ca(2+)-adenosine triphosphatase, succinic dehydrogenase and cytochrome C oxidase were markedly enhanced by OA treatment. The ratio of unsaturated/saturated fattyacid in OA-treated fruit was significantly higher than that in control fruit. These results suggest that the alleviation in chilling injury by OA may be due to enhanced enzyme activities related to energy metabolism and higher levels of energy status and unsaturated/saturated fattyacid ratio.

Listeria monocytogenes is a food-borne pathogen that grows at refrigeration temperatures and increases its content of anteiso-C15:0 fattyacid, which is believed to be a homeoviscous adaptation to ensure membrane fluidity, at these temperatures. As a possible novel approach for control of the growth of the organism, the influences of various fattyacid precursors, including branched-chain amino acids and branched- and straight-chain carboxylic acids, some of which are also well-established food preservatives, on the growth and fattyacid composition of the organism at 37°C and 10°C were studied in order to investigate whether the organism could be made to synthesize fattyacids that would result in impaired growth at low temperatures. The results indicate that the fattyacid composition of L. monocytogenes could be modulated by the feeding of branched-chain amino acid, C4, C5, and C6 branched-chain carboxylic acid, and C3 and C4 straight-chain carboxylic acidfattyacid precursors, but the growth-inhibitory effects of several preservatives were independent of effects on fattyacid composition, which were minor in the case of preservatives metabolized via acetyl coenzyme A. The ability of a precursor to modify fattyacid composition was probably a reflection of the substrate specificities of the first enzyme, FabH, in the condensation of primers of fattyacid biosynthesis with malonyl acyl carrier protein. PMID:20048057

Omega fattyacids are recognized as key nutrients for healthier ageing. Lipases are used to release ω-3 fattyacids from oils for preparing enriched ω-3 fattyacid supplements. However, use of lipases in enrichment of ω-3 fattyacids is limited due to their insufficient specificity for ω-3 fattyacids. In this study use of phospholipase A1 (PLA1), which possesses both sn-1 specific activity on phospholipids and lipase activity, was explored for hydrolysis of ω-3 fattyacids from anchovy oil. Substrate specificity of PLA1 from Thermomyces lenuginosus was initially tested with synthetic p-nitrophenyl esters along with a lipase from Bacillus subtilis (BSL), as a lipase control. Gas chromatographic characterization of the hydrolysate obtained upon treatment of anchovy oil with these enzymes indicated a selective retention of ω-3 fattyacids in the triglyceride fraction by PLA1 and not by BSL. 13C NMR spectroscopy based position analysis of fattyacids in enzyme treated and untreated samples indicated that PLA1 preferably retained ω-3 fattyacids in oil, while saturated fattyacids were hydrolysed irrespective of their position. Hydrolysis of structured triglyceride,1,3-dioleoyl-2-palmitoylglycerol, suggested that both the enzymes hydrolyse the fattyacids at both the positions. The observed discrimination against ω-3 fattyacids by PLA1 appears to be due to its fattyacid selectivity rather than positional specificity. These studies suggest that PLA1 could be used as a potential enzyme for selective concentrationof ω-3 fattyacids.

Recent studies suggest that dairy operations may be a major source of non-methane volatile organic compounds in dairy-intensive regions such as Central California, with short chain carboxylic acids (volatile fattyacids or VFAs) as the major components. Emissions of four VFAs (acetic acid, propanoic acid, butanoic acid and hexanoic acid) were measured from two feed sources (silage and total mixed rations (TMR)) at six Central California Dairies over a fifteen-month period. Measurements were made using a combination of flux chambers, solid phase micro-extraction fibers coupled to gas chromatography mass spectrometry (SPME/GC-MS) and infra-red photoaccoustic detection (IR-PAD for acetic acid only). The relationship between acetic acid emissions, source surface temperature and four sample composition factors (acetic acid content, ammonia-nitrogen content, water content and pH) was also investigated. As observed previously, acetic acid dominates the VFA emissions. Fluxes measured by IR-PAD were systematically lower than SPME/GC-MS measurements by a factor of two. High signals in field blanks prevented emissions from animal waste sources (flush lane, bedding, open lot) from being quantified. Acetic acid emissions from feed sources are positively correlated with surface temperature and acetic acid content. The measurements were used to derive a relationship between surface temperature, acetic acid content and the acetic acid flux. The equation derived from SPME/GC-MS measurements predicts estimated annual average acetic acid emissions of (0.7 + 1/-0.4) g m -2 h -1 from silage and (0.2 + 0.3/-0.1) g m -2 h -1 from TMR using annually averaged acetic acid content and meteorological data. However, during the summer months, fluxes may be several times higher than these values.

Oxylipins or oxidized fattyacids are a group of molecules found to play a role in signaling in many different cell types. These fattyacid derivatives have ancient evolutionary origins as signaling molecules and are ideal candidates for inter-kingdom communication. This review discusses examples of the ability of organisms from different kingdoms to "listen" and respond to oxylipin signals during interactions. The interactions that will be looked at are signaling between animals and plants; between animals and fungi; between animals and bacteria and between plants and fungi. This will aid in understanding these interactions, which often have implications in ecology, agriculture as well as human and animal health.

Background Mitochondrial fattyacid β-oxidation disorders (FAODs) are a heterogeneous group of defects in fattyacid transport and mitochondrial β-oxidation. They are inherited as autosomal recessive disorders and have a wide range of clinical presentations. Summary The background information and case report provide important insight into mitochondrial FAODs. The article provides a wealth of information describing the scope of these disorders. Key Messages This article presents a typical case of medium chain acyl-CoA dehydrogenase deficiency and summarizes the pathophysiology, clinical presentation, diagnosis and treatment of mitochondrial FAODs. PMID:27536022

Mounting data show that fattyacids (FA) and fattyacid synthase (FAS) function could be potential targets for multiple myeloma (MM) therapy. Our study aimed at comparing the FA composition of erythrocyte membranes of MM patients and healthy controls. MM patients had higher saturated FA and n-6 polyunsaturated FA (PUFA) and lower monounsaturated, n-3 PUFA and trans-FA indices than controls. The n-3/n-6 PUFA ratio was lower in MM patients and there was distinct clustering of variants of individual FA in MM patients. The FA content of erythrocyte membrane could serve as a diagnostic and/or predictive biomarker in MM.

A detailed study of the cultural characteristics and cellular fattyacid composition of 27 isolates of Corynebacterium acnes was performed to establish the properties by which this organism may be identified and characterized. The fattyacids were extracted directly from whole cells and examined as methyl esters by gas-liquid chromatography. Each strain possessed a similar fattyacid profile which was characterized by a large percentage of C15 branched-chain acid. Uniformity in certain biochemical reactions and cultural characteristics was also observed. All strains were catalase-positive, nonmotile, and urease-negative, reduced nitrate, liquefied gelatin, failed to hydrolyze esculin and starch, and gave a positive methyl red test. Glucose, fructose, and glycerol were fermented, but not lactose, salicin, sucrose, maltose, xylose, or arabinose. Production of hydrogen sulfide and indole, fermentation of mannitol, and hemolytic activity were variable characteristics. Two species of the genus Propionibacterium were also tested and found to be similar to C. acnes both in cultural characteristics and fattyacid composition. The results strengthen previous suggestions that C. acnes should be classified in the genus Propionibacterium.

Sport injuries are common and costly for the professional athlete, the "weekend warrior," and the community. Acute injuries are treated according to current guidelines with the aim of bringing the athlete back into the arena. These guidelines have not taken into account new scientific results of the inflammatory process following a trauma. The 4 hallmarks of inflammation, namely, pain, swelling, redness, and heat, are results of an adequate inflammatory response with the aim of bringing the affected tissue back to restitution (Latin: restitutio ad integrum). Cooling of the affected limb and anti-inflammatory drugs are widely used but may deter healing. The healing process is governed by fattyacids of the omega-3 and omega-6 series. In order to facilitate healing, these fattyacids have to be present in significant amounts in the affected tissues before the trauma occurs. This is particularly relevant for marine omega-3 fattyacids, which are often running low due to insignificant intake of seafood, common in individuals practicing sports. High-energy sports often lead to head and brain trauma. Continuous head traumata may even result in later mental defects. Saturation of brain cells with omega-3 fattyacids, in particular docosahexaenoic acid (DHA), may facilitate healing after brain trauma, thereby counteracting negative long-term results. The present understanding of a normal inflammatory process leading to restitution will be discussed along with data from recent scientific trials.

Previous studies have demonstrated that the branched-chain fattyacid anteiso-C15:0 plays a critical role in the growth of Listeria monocytogenes at low temperatures by ensuring sufficient membrane fluidity. Studies utilizing a chemically defined minimal medium revealed that the anteiso fattyacid precursor isoleucine largely determined the fattyacid profile and fattyacid response of the organism to lowered growth temperature. When isoleucine was sufficient, the fattyacid profile was very uniform, with anteiso fattyacids comprising up to 95% of total fattyacid, and the major fattyacid adjustment to low temperature was fattyacid chain shortening, which resulted in an increase of anteiso-C15:0 solely at the expense of anteiso-C17:0. When isoleucine was not supplied, the fattyacid profile became more complex and was readily modified by leucine, which resulted in a significant increase of corresponding iso fattyacids and an inability to grow at 10°C. Under this condition, the increase of anteiso-C15:0 at low temperature resulted from the combined effect of increasing the anteiso:iso ratio and chain shortening. A branched-chain α-keto acid dehydrogenase-defective strain largely lost the ability to increase the anteiso:iso ratio. Cerulenin, an inhibitor of β-ketoacyl-acyl carrier protein synthase (FabF), induced a similar fattyacid chain shortening as low temperature did. We propose that the anteiso precursor preferences of enzymes in the branched-chain fattyacid biosynthesis pathway ensure a high production of anteiso fattyacids, and cold-regulated chain shortening results in a further increase of anteiso-C15:0 at the expense of anteiso-C17:0. PMID:16332779

... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Glyceryl-lacto esters of fattyacids. 172.852... § 172.852 Glyceryl-lacto esters of fattyacids. Glyceryl-lacto esters of fattyacids (the lactic acid esters of mono- and diglycerides) may be safely used in food in accordance with the following...

One goal of green chemistry is the production of industrially useful fattyacids (FAs) in crop plants. We focus on the engineering of industrial FAs, specifically hydroxy fattyacids (HFA) and conjugated polyenoic fattyacids (a-eleostearic acid, ESA), using Arabidopsis (Arabidopsis thaliana) as a m...

This study was conducted to determine the effect of calcium salts of fattyacids (CSFA) on fattyacid profile of milk of "Sahiwal" cows and suitability of milk with modified fattyacids in the formulation of ice cream. Fattyacid profile of cow milk was modified by feeding CSFA to eighteen randomly stratified "Sahiwal" cows of first and early lactation divided into three groups. CSFA were offered at two different levels i.e. T1 (150 g per cow per day) T2 (300 g per cow per day) both treatments were compared with a control (T0) without any addition of calcium salts of fattyacids. Iso caloric and iso nitrogenous feeds were given to both experimental groups and control. Concentrations of short chain fattyacids in T0, T1 and T2 were 9.85 ± 0.48a, 8.8 ± 0.24b and 7.1 ± 0.37c %, respectively and the concentrations of C18:1 and C18:2 increased (P fatty acids profile) in ice cream did not have any adverse effect on pH, acidity and compositional attributes of ice cream. Viscosity of T1 was 67.94 ± 3.77a as compared to (T0) control 68.75 ± 2.46a (CP). Firmness of experimental samples and control were almost similar (P > 0.05) overall acceptability score of T2 was 7.1 ± 0.28b out of 9 (total score) which was more than 78 ± 2.92 %. It was concluded that CSFA may be successfully incorporated up to T2 level (300 g per cow per day) into the feed of "Sahiwal" cows to produce milk with higher content of unsaturated fattyacids and it may be used in the formulation of ice cream with acceptable sensory characteristics and increased health benefits.

We developed and validated an efficient and robust method for the simultaneous quantification of 44 fattyacid species in human plasma via GC-TOF-MS. The method is characterized by its robustness, accuracy and precision covering a wide range of fattyacid species with various saturation degrees including short chain fattyacids (beginning with FA 4:0) and long chain fattyacids (up to FA 32:0). The fattyacids were methylated prior to analyses and subsequently detected as fattyacid methyl esters by means of GC-TOF-MS. A highly substituted polar column allowed the separation of geometrical and positional isomers of fattyacid species. The method was applied to plasma samples of a strictly diet controlled clinical smoking cessation study including 39 smokers followed over the course of three months after having quit. Statistical significant alterations within the fattyacid profile were observed when comparing the baseline (subjects still smoking) with one week, one month and three months of smoking cessation. After 3 months of smoking cessation, a partial recovery of alterations in the fattyacid profile evoked by smoking was observed. In conclusion, the developed fattyacid profiling method using GC-TOF-MS has proven as a reliable tool for the quantitative determination of 44 individual fattyacid species within clinical studies.

We report the dispersions of a fattyacid and hydroxyl derivative salts in aqueous solutions that were further used to produce foams and emulsions. The tetrabutyl-ammonium salts of palmitic acid, 12-hydroxy stearic acid, and omega-hydroxy palmitic acid formed isotropic solutions of micelles, whereas the ethanolamine salts of the same acids formed turbid birefringent lamellar solutions. The structure and dimension of those phases were confirmed by small-angle neutron scattering and NMR. Micelles exhibited a surprisingly small radius of about 20 A, even for hydroxyl fattyacids, suggesting the formation of hydrogen bonds between lipids in the core of the micelles. In the case of ethanolamine salts of palmitic and 12-hydroxy stearic acids, the lipids were arranged in bilayers, with a phase transition from gel to fluid upon heating, whereas for omega-hydroxy palmitic acid, monolayers formed in accordance with the bola shape of this lipid. Foams and emulsions produced from ethanolamine salt solutions were more stable than those obtained from tetrabutyl-ammonium salt solutions. We discuss these results in terms of counterion size, lipid molecular shape, and membrane curvature.

To clarify the influence of the fattyacid composition of sebum in acne vulgaris, we investigated the amounts and fattyacid compositions of triglycerides (TG) and free fattyacids (FFA), and the amounts of cutaneous superficial Propionibacterium acnes in acne patients and healthy subjects. The foreheads of 18 female patients, 10 male patients, 10 healthy females and 10 healthy males were studied in a Japanese population. There were significant differences in the amounts of sebum, TG and cutaneous superficial P. acnes, as well as the fattyacid compositions of TG and FFA between acne patients and healthy subjects in females. Their fattyacid compositions were correlated with the amount of TG with or without acne. It was clarified that the fattyacid compositions of TG and FFA depended on the amount of TG, and there were no differences in the fattyacid composition in the presence and absence of acne.

N-3 Polyunsaturated fattyacids have been shown to have potential beneficial effects for chronic diseases including cancer, insulin resistance and cardiovascular disease. Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in particular have been studied extensively, whereas substantive evidence for a biological role for the precursor, alpha-linolenic acid (ALA), is lacking. It is not enough to assume that ALA exerts effects through conversion to EPA and DHA, as the process is highly inefficient in humans. Thus, clarification of ALA's involvement in health and disease is essential, as it is the principle n-3 polyunsaturated fattyacid consumed in the North American diet and intakes of EPA and DHA are typically very low. There is evidence suggesting that ALA, EPA and DHA have specific and potentially independent effects on chronic disease. Therefore, this review will assess our current understanding of the differential effects of ALA, EPA and DHA on cancer, insulin resistance, and cardiovascular disease. Potential mechanisms of action will also be reviewed. Overall, a better understanding of the individual role for ALA, EPA and DHA is needed in order to make appropriate dietary recommendations regarding n-3 polyunsaturated fattyacid consumption. PMID:19664246

In this work new types of hydrophobically modified maltodextrin were prepared by enzyme-catalyzed reaction of maltodextrin and three fattyacids: decanoic acid (C-10), lauric acid (C-12) and palmitic acid (C-16). Lipase obtained from Thermomyces lanuginosus was found to be a useful biocatalyst in the maltodextrin esterification. Esterified maltodextrin with a degree of substitution (DS) 0.015-0.084 was prepared at the optimum conditions of 60 °C for 4 h. The DS was found to be at its highest when maltodextrin and fattyacids were taken in the ratio 1:0.5. The functional properties of these esterified maltodextrin were investigated. All esterified maltodextrin did not completely dissolve in water. Esterified maltodextrin at a concentration of 25% (w/w) exhibited Newtonian flow behavior similar to that of native maltodextrin. Esterified maltodextrin had a higher viscosity compare to native maltodextrin. X-ray diffraction pattern of esterified maltodextrin indicated crystallization of the fattyacid side chains. The thermal stability of esterified maltodextrin was checked by differential scanning calorimetry (DSC). Esterified maltodextrin was then used as an emulsifier to make n-hexadecane O/W emulsions. The emulsions were characterized according to their oil droplet characteristics and emulsification index.

Long chain fattyacids (LCFA) serve as energy sources, components of cell membranes, and precursors for signalling molecules. Here we show that these biological compounds also regulate gene expression and that they do so by controlling the transcriptional activities of the retinoic acid (RA)-activated nuclear receptors RAR and PPARβ/δ. The data indicate that these activities of LCFA are mediated by FABP5 which delivers ligands from the cytosol to nuclear PPARβ/δ. Both saturated and unsaturated LCFA (SLCFA, ULCFA) bind to FABP5, thereby displacing RA and diverting it to RAR. However, while SLCFA inhibit, ULCFA activate the FABP5/PPARβ/δ pathway. We show further that, by concomitantly promoting activation of RAR and inhibiting the activation of PPARβ/δ, SLCFA suppress the oncogenic properties of FABP5-expressing carcinoma cells in cultured cells and in vivo. The observations suggest that compounds that inhibit FABP5 may constitute a new class of drugs for therapy of certain types of cancer. PMID:26592976

Long chain fattyacids (LCFA) serve as energy sources, components of cell membranes and precursors for signalling molecules. Here we show that these biological compounds also regulate gene expression and that they do so by controlling the transcriptional activities of the retinoic acid (RA)-activated nuclear receptors RAR and PPARβ/δ. The data indicate that these activities of LCFA are mediated by FABP5, which delivers ligands from the cytosol to nuclear PPARβ/δ. Both saturated and unsaturated LCFA (SLCFA, ULCFA) bind to FABP5, thereby displacing RA and diverting it to RAR. However, while SLCFA inhibit, ULCFA activate the FABP5/PPARβ/δ pathway. We show further that, by concomitantly promoting the activation of RAR and inhibiting the activation of PPARβ/δ, SLCFA suppress the oncogenic properties of FABP5-expressing carcinoma cells in cultured cells and in vivo. The observations suggest that compounds that inhibit FABP5 may constitute a new class of drugs for therapy of certain types of cancer.

The aim of this study is the first time demonstration of cis-12 regio-selective linoleate double-bond hydratase. Hydroxylation of fattyacids, abundant feedstock in nature, is an emerging alternative route for many petroleum replaceable products thorough hydroxy fattyacids, carboxylic acids, and lactones. However, chemical route for selective hydroxylation is still quite challenging owing to low selectivity and many environmental concerns. Hydroxylation of fattyacids by hydroxy fattyacid forming enzymes is an important route for selective biocatalytic oxyfunctionalization of fattyacids. Therefore, novel fattyacid hydroxylation enzymes should be discovered. The two hydratase genes of Lactobacillus acidophilus were identified by genomic analysis, and the expressed two recombinant hydratases were identified as cis-9 and cis-12 double-bond selective linoleate hydratases by in vitro functional validation, including the identification of products and the determination of regio-selectivity, substrate specificity, and kinetic parameters. The two different linoleate hydratases were the involved enzymes in the 10,13-dihydroxyoctadecanoic acid biosynthesis. Linoleate 13-hydratase (LHT-13) selectively converted 10 mM linoleic acid to 13S-hydroxy-9(Z)-octadecenoic acid with high titer (8.1 mM) and yield (81%). Our study will expand knowledge for microbial fattyacid-hydroxylation enzymes and facilitate the designed production of the regio-selective hydroxy fattyacids for useful chemicals from polyunsaturated fattyacid feedstocks.

Cooling strategies for pumping of raw milk were evaluated. Milk was pumped for 450 s at 31 degrees C, or pumped after cooling to 4 degrees C and subsequently subjected to various incubation times. Two types of milk were used; i.e. milk from cows fed a diet high in saturated fat supplements resulting in significantly larger milk fat globules than the other type of milk which comes from cows fed a low-fat diet that stimulates high de novo fat synthesis. The content of liquid fat was determined by low-field 1H NMR, which showed that milk from cows given the saturated fat diet also contained less liquid fat at both 4 degrees and 31 degrees C than the other type of milk. This can be ascribed to the differences in the fattyacid composition of the milk as a result of the fattyacid composition of the diets. After pumping of the milk at 31 degrees C, measurement of fat globule size distribution revealed a significant coalescence of milk fat globules in the milk obtained from the saturated fat diet due to pumping. Pumping at 4 degrees C or pumping the other type of milk did not result in coalescence of milk fat globules. Formation of free fattyacids increased significantly in both types of milk by pumping at 31 degrees C. Cooling the milk to 4 degrees C immediately before pumping inhibited an increased content of free fattyacids. However, when the milk was incubated at 4 degrees C for 60 min after cooling and then subjected to pumping, a significant increase in the formation of free fattyacids was observed in both types of milk. It is suggested that this increase in free fattyacids is caused by transition of polymorphic crystal forms or higher level of attached lipoprotein lipases to the milk fat globule before pumping.

A soluble fattyacid-binding protein (FABP), mol wt ∼ 12,000 is present in intestinal mucosa and other tissues that utilize fattyacids, including liver, myocardium, adipose, and kidney. This protein binds long chain fattyacids both in vivo and in vitro. FABP was isolated from rat intestine by gel filtration and isoelectric focusing. It showed a reaction of complete immunochemical identity with proteins in the 12,000 mol wt fattyacid-binding fractions of liver, myocardium, and adipose tissue supernates. (The presence of immunochemically nonidentical 12,000 mol wt FABP in these tissues is not excluded.) By quantitative radial immunodiffusion, supernatant FABP concentration in mucosa from proximal and middle thirds of jejuno-ileum significantly exceeded that in distal third, duodenum, and liver, expressed as micrograms per milligram soluble protein, micrograms per gram DNA, and micrograms per gram tissue. FABP concentration in villi was approximately three times greater than in crypts. Small quantities of FABP were present in washed nuclei-cell membrane, mitochondrial and microsomal fractions. However, the amount of FABP solubilized per milligram membrane protein was similar for all particulate fractions, and total membrane-associated FABP was only about 16% of supernatant FABP. Intestinal FABP concentration was significantly greater in animals maintained on high fat diets than on low fat; saturated and unsaturated fat diets did not differ greatly in this regard. The preponderance of FABP in villi from proximal and middle intestine, its ability to bind fattyacids in vivo as well as in vitro, and its response to changes in dietary fat intake support the concept that this protein participates in cellular fattyacid transport during fat absorption. Identical or closely related 12,000 mol wt proteins may serve similar functions in other tissues. Images PMID:4211161

Microbial fattyacids are an attractive source of precursors for a variety of renewable commodity chemicals such as alkanes, alcohols, and biofuels. Rerouting lipid biosynthesis into free fattyacid production can be toxic, however, due to alterations of membrane lipid composition. Here we find that membrane lipid composition can be altered by the direct incorporation of medium-chain fattyacids into lipids via the Aas pathway in cells expressing the medium-chain thioesterase from Umbellularia californica (BTE). We find that deletion of the aas gene and sequestering exported fattyacids reduces medium-chain fattyacid toxicity, partially restores normal lipid composition, and improves medium-chain fattyacid yields.

The gas chromatographic analysis of fattyacids has attracted considerable interest. In this analysis, the common derivatives of fattyacids, such as fattyacid methyl esters, can be detected using a flame ionization detector and the mass spectra can indicate the true structure of fattyacids. This paper reviews gas chromatographic methods for obtaining fattyacids from marine organisms. The stationary phase and detector for applications in gas chromatography are discussed. This article also reviews the components of fattyacids in marine animals, marine plants and marine microorganisms.

The catalytic performance and recoverability of several homogeneous acid catalysts (hydrochloric, sulfuric, and nitric acids) for the esterification of enzyme-hydrolyzed free fattyacid (FFA) and methanol were studied. Although all tested catalysts drove the reaction to a high yield, hydrochloric acid was the only catalyst that could be considerably recovered and reused. The kinetics of the esterification reaction catalyzed by hydrochloric acid was investigated under varying catalyst loading (0.1-1M), reaction temperature (303-343K), and methanol/FFA molar ratio (1:1-20:1). In addition, a pseudo-homogeneous kinetic model incorporating the above factors was developed. A good agreement (r(2)=0.98) between the experimental and calculated data was obtained, thus proving the reliability of the model. Furthermore, the reusability of hydrochloric acid in FFA esterification can be predicted by the developed model. The recoverable hydrochloric acid achieved high yields of FFA esterification within five times of reuse.

Objectives This study assessed the antibacterial activity of short-, medium-, and long-chain fattyacids against various oral microorganisms. Methods The short-chain fattyacids [formic acid (C1), acetic acid (C2), propionic acid (C3), butyric acid (C4), isobutyric acid (C4), isovaleric acid (C5), hexanoic acid (C6)], medium-chain fattyacids [octanoic acid (C8), capric acid (C10), lauric acid (12)], and long-chain fattyacids [myristic acid (C14), palmitic acid (C16)], were investigated for antimicrobial activity against Streptococcus mutans, S. gordonii, S. sanguis, Candida albicans, Aggregatibacter actinomycetemcomitans, Fusobacterium nucleatum, and Porphyromonas gingivalis. Results The data demonstrated that the fattyacids exhibited patterns of inhibition against oral bacteria with some specificity that appeared related more to the bacterial species that the general structural characteristics of the microorganism. As a group the fattyacids were much less effective against C. albicans than the oral bacteria, with effectiveness limited to hexanoic, octanoic, and lauric acids. Formic acid, capric, and lauric acids were broadly inhibitory for the bacteria. Interestingly, fattyacids that are produced at metabolic end-products by a number of these bacteria, were specifically inactive against the producing species, while substantially inhibiting the growth of other oral microorganisms. Conclusions The results indicate that the antimicrobial activity of short-chain fattyacids (SCFAs), medium-chain fattyacids (MCFAs), long-chain fattyacids (LCFAs) could influence the microbial ecology in the oral cavity via at least 2 potential pathways. First, the agents delivered exogenously as therapeutic adjuncts could be packaged to enhance a microbial-regulatory environment in the subgingival sulcus. Second, it would be the intrinsic nature of these fattyacid inhibitors in contributing to the characteristics of the microbial biofilms, their evolution, and emergence of

Long-chain polyunsaturated fattyacids are essential for human nutrition. The number of double bonds determines whether a given fattyacid is termed two, three, or x times unsaturated. Depending on the distance of the first double bond from the fattyacid's methyl group, one distinguishes omega-3 fattyacids from omega-6 fattyacids. While the use of gamma linolenic acid, a long-chain fattyacid of the omega-6 family, has proven unsuccessful in the prevention or treatment of atopic dermatitis, supplementation of long-chain omega-3 fattyacids may represent a promising approach in the prevention of allergic disorders, especially atopic dermatitis. Whether the concept of long-chain omega-3 fattyacid administration will also become established in a therapeutic setting, depends on whether the beneficial effects observed so far can be substantiated in randomized controlled intervention studies.

Okra has different uses as a food and a remedy in traditional medicine. Since it produces many seeds, distribution of the plant is also quite easy. Although seed oil yield is low (4.7%), since the linoleic acid composition of the seed oil is quiet high (67.5%), it can still be used as a source of (UNSAT) unsaturated fattyacids. In this study, samples of okra grown in four different locations were analyzed to measure fattyacid and amino acid compositions. The content of the lipid extraction ranged from 4.34% to 4.52% on a dry weight basis. Quantitatively, the main okra fattyacids were palmitic acid (29.18-43.26%), linoleic acid (32.22-43.07%), linolenic acid (6.79-12.34%), stearic acid (6.36-7.73%), oleic acid (4.31-6.98%), arachidic acid (ND-3.48%), margaric acid (1.44-2.16%), pentadecylic acid (0.63-0.92%), and myristic acid (0.21-0.49%). Aspartic acid, proline, and glutamic acids were the main amino acids in okra pods, while cysteine and tyrosine were the minor amino acids. Statistical methods revealed how the fattyacid and amino acid contents in okra may be affected by the sampling location.

We have reviewed literature regarding the effects of n-3 polyunsaturated fattyacids (PUFA) on risk factors for atherosclerosis in human subjects. Dietary intervention with long chain n-3 PUFA decreased some risk factor (s) for atherosclerosis in most human studies reviewed. These benefits resulted ...

A radiolabeled long chain fattyacid for heart imaging that has dimethyl branching at one of the carbons of the chain which inhibits the extent to which oxidation can occur. The closer to the carboxyl the branching is positioned, the more limited the oxidation, thereby resulting in prolonged retention of the radiolabeled compound in the heart.

A bisamide-bisthiol ligand containing fattyacid substituted thiol useful for producing Tc-labelled radiodiagnostic imaging agents is described. The ligand forms a complex with the radionuclide .sup.99m Tc suitable for administration as a radiopharmaceutical to obtain images of the heart for diagnosis of myocardial disfunction.

P Lesquerella [Physaria fendleri (A. Gray)], formerly Lesquerella fendleri, (Brassicaceae), being developed as a new industrial oilseed crop in the southwestern region of the United States, is valued for its unusual hydroxy fattyacid (HFA) in seed. The majority of HFA in lesquerella is lesquerolic...

Necrotizing enterocolitis, characterized by sudden onset and rapid progression, remains the most significant gastrointestinal disorder among premature infants. In seeking a predictive biomarker, we found intestinal fattyacid binding protein, an indicator of enterocyte damage, was substantially increased within three and seven days before the diagnosis of necrotizing enterocolitis.

Free fattyacids and monoglycerides have long been known to possess broad-spectrum antibacterial activity that is based on lytic behavior against bacterial cell membranes. Considering the growing challenges of drug-resistant bacteria and the need for new classes of antibiotics, the wide prevalence, affordable cost, and broad spectrum of fattyacids and monoglycerides make them attractive agents to develop for healthcare and biotechnology applications. The aim of this review is to provide a brief introduction to the history of antimicrobial lipids and their current status and challenges, and to present a detailed discussion of ongoing research efforts to develop nanotechnology formulations of fattyacids and monoglycerides that enable superior in vitro and in vivo performance. Examples of nano-emulsions, liposomes, solid lipid nanoparticles, and controlled release hydrogels are presented in order to highlight the potential that lies ahead for fattyacids and monoglycerides as next-generation antibacterial solutions. Possible application routes and future directions in research and development are also discussed.

I determined the fattyacid composition of subcutaneous, abdominal, visceral, and leg saddle depots in adult female Canada Geese (Branta canadensis) wintering in north-central Missouri during October 1984-March 1985. Mean levels of C14:0, C16:0, C16:1, C18:0, C18:1, C18:2, and C18:3 generally were highest in the subcutaneous and abdominal depots. The ratio of saturated to unsaturated fats was highest in the leg saddle depot and lowest in the abdominal depot. I also assessed the differences among sexes, seasons, and years in fattyacid composition of abdominal fat depots in adult geese collected during October-March, 1985-1987. Adult females had consistently higher levels of C14:0 in abdominal depots than males. Fattyacid composition of the abdominal depot differed among years but not by season. In the abdominal depot, C14:0, C16:0, C16:1, and C18:1 were higher in 1986-1987 compared with the previous two years, whereas C18:3 was highest in 1984-1985. Differences among years reflected changes in winter diet. Fattyacids of wintering geese were similar to those previously found in breeding Canada Geese.

Inflammation is believed to play a central role in many of the chronic diseases that characterize modern society. In the past decade, our understanding of how dietary fats affect our immune system and subsequently our inflammatory status has grown considerably. There are compelling data showing that high-fat meals promote endotoxin [e.g., lipopolysaccharide (LPS)] translocation into the bloodstream, stimulating innate immune cells and leading to a transient postprandial inflammatory response. The nature of this effect is influenced by the amount and type of fat consumed. The role of various dietary constituents, including fats, on gut microflora and subsequent health outcomes in the host is another exciting and novel area of inquiry. The impact of specific fattyacids on inflammation may be central to how dietary fats affect health. Three key fatty acid–inflammation interactions are briefly described. First, the evidence suggests that saturated fattyacids induce inflammation in part by mimicking the actions of LPS. Second, the often-repeated claim that dietary linoleic acid promotes inflammation was not supported in a recent systematic review of the evidence. Third, an explanation is offered for why omega-3 (n–3) polyunsaturated fattyacids are so much less anti-inflammatory in humans than in mice. The article closes with a cautionary tale from the genomic literature that illustrates why extrapolating the results from inflammation studies in mice to humans is problematic. PMID:25979502

Drosophila melanogaster has been considered an ideal model organism to investigate human diseases and genetic pathways. Whether Drosophila is an ideal model for nutrigenomics, especially for fattyacid metabolism, however, remains to be illustrated. This study was to examine the metabolism of C20 an...

Antimicrobial peptides are small molecules that play a crucial role in innate immunity in multi-cellular organisms, and usually expressed and secreted constantly at basal levels to prevent infection, but local production can be augmented upon an infection. The clock is ticking as rising antibiotic abuse has led to the emergence of many drug resistance bacteria. Due to their broad spectrum antibiotic and antifungal activities as well as anti-viral and anti-tumor activities, efforts are being made to develop antimicrobial peptides into future microbial agents. This article describes some of the recent patents on antimicrobial peptides with fattyacid conjugation. Potency and selectivity of antimicrobial peptide can be modulated with fattyacid tails of variable length. Interaction between membranes and antimicrobial peptides was affected by fattyacid conjugation. At concentrations above the critical miscelle concentration (CMC), propensity of solution selfassembly hampered binding of the peptide to cell membranes. Overall, fattyacid conjugation has enhanced the activities of antimicrobial peptides, and occasionally it rendered inactive antimicrobial peptides to be bioactive. Antimicrobial peptides can not only be used as medicine but also as food additives.

In all organisms, fattyacid synthesis is achieved in variations of a common cyclic reaction pathway by stepwise, iterative elongation of precursors with two-carbon extender units. In bacteria, all individual reaction steps are carried out by monofunctional dissociated enzymes, whereas in eukaryotes the fattyacid synthases (FASs) have evolved into large multifunctional enzymes that integrate the whole process of fattyacid synthesis. During the last few years, important advances in understanding the structural and functional organization of eukaryotic FASs have been made through a combination of biochemical, electron microscopic and X-ray crystallographic approaches. They have revealed the strikingly different architectures of the two distinct types of eukaryotic FASs, the fungal and the animal enzyme system. Fungal FAS is a 2·6 MDa α₆β₆ heterododecamer with a barrel shape enclosing two large chambers, each containing three sets of active sites separated by a central wheel-like structure. It represents a highly specialized micro-compartment strictly optimized for the production of saturated fattyacids. In contrast, the animal FAS is a 540 kDa X-shaped homodimer with two lateral reaction clefts characterized by a modular domain architecture and large extent of conformational flexibility that appears to contribute to catalytic efficiency.

A new catalytic route to bio-olefins from unsaturated fattyacids will be described. At the heart of the process, the catalyst apparently functions in a tandem mode by both dynamically isomerizing the positions of double bonds in an aliphatic chain and, subsequently, decarboxylating specific isomers...

Fattyacids, which are essential cell membrane constituents and fuel storage molecules, are thought to share a common evolutionary origin with polyketide toxins in eukaryotes. While fattyacids are primary metabolic products, polyketide toxins are secondary metabolites that are involved in ecologically relevant processes, such as chemical defence, and produce the adverse effects of harmful algal blooms. Selection pressures on such compounds may be different, resulting in differing evolutionary histories. Surprisingly, some studies of dinoflagellates have suggested that the same enzymes may catalyse these processes. Here we show the presence and evolutionary distinctiveness of genes encoding six key enzymes essential for fattyacid production in 13 eukaryotic lineages for which no previous sequence data were available (alveolates: dinoflagellates, Vitrella, Chromera; stramenopiles: bolidophytes, chrysophytes, pelagophytes, raphidophytes, dictyochophytes, pinguiophytes, xanthophytes; Rhizaria: chlorarachniophytes, haplosporida; euglenids) and 8 other lineages (apicomplexans, bacillariophytes, synurophytes, cryptophytes, haptophytes, chlorophyceans, prasinophytes, trebouxiophytes). The phylogeny of fattyacid synthase genes reflects the evolutionary history of the organism, indicating selection to maintain conserved functionality. In contrast, polyketide synthase gene families are highly expanded in dinoflagellates and haptophytes, suggesting relaxed constraints in their evolutionary history, while completely absent from some protist lineages. This demonstrates a vast potential for the production of bioactive polyketide compounds in some lineages of microbial eukaryotes, indicating that the evolution of these compounds may have played an important role in their ecological success. PMID:26784357

This paper reports the incorporation of an alpha-methylene unit into fattyacid skeletons. Since the new olefin is conjugated with the carboxylate, it is susceptible to 1,4- (Michael) additions. We have used multifunctional thiols and amines for additions at the methylene. The resulting products ...

Previous research has indicated that long-chain fattyacids can bind myoglobin (Mb) in an oxygen dependent manner. This suggests that Oxy-Mb may play an important role in fuel delivery in Mb-rich muscle fibers (e.g., type I fibers and cardiomyocytes), and raises the possibility that Mb also serves ...

Lipids are essential components of a living organism as energy source but also as constituent of the membrane lipid bilayer. In addition fattyacid (FA) derivatives interact with many signaling pathways. FAs have amphipathic properties and therefore require being associated to protein for both transport and intracellular trafficking. Here we will focus on several FA handling proteins, among which the fattyacid translocase/CD36 (FAT/CD36), members of fattyacid transport proteins (FATPs), and lipid chaperones fattyacid-binding proteins (FABPs). A decade of extensive studies has helped decipher the mechanism of action of these proteins in peripheral tissue with high lipid metabolism. However, considerably less information is available regarding their role in the brain, despite the high lipid content of this tissue. This review will primarily focus on the recent studies that have highlighted the crucial role of lipid handling proteins in brain FA transport, neuronal differentiation and development, cognitive processes and brain diseases. Finally a special focus will be made on the recent studies that have revealed the role of FAT/CD36 in brain lipid sensing and nervous control of energy balance. PMID:23060810

A method for enhancing amidohydrolase activity of FattyAcid Amide Hydrolase (FAAH) is disclosed. The method comprising administering a phenoxyacylethanolamide that causes the enhanced activity. The enhanced activity can have numerous effects on biological organisms including, for example, enhancing the growth of certain seedlings. The subject matter disclosed herein relates to enhancers of amidohydrolase activity.

Research dating back to the 1950s reported an association between the consumption of saturated fattyacids (SFAs) and risk of coronary heart disease. Recent epidemiological evidence, however, challenges these findings. It is well accepted that the consumption of SFAs increases low-density lipoprotei...

Supported metal catalysts containing 5 wt% Pd on silica, alumina, and activated carbon were evaluated for liquid-phase deoxygenation of stearic (octadecanoic), lauric (dodecanoic), and capric (decanoic) acids under 5 % H-2 at 300 A degrees C and 15 atm. On-line quadrupole mass spectrometry (QMS) was used to measure CO + CO2 yield, CO2 selectivity, H-2 consumption, and initial decarboxylation rate. Post-reaction analysis of liquid products by gas chromatography was used to determine n-alkane yields. The Pd/C catalyst was highly active and selective for stearic acid (SA) decarboxylation under these conditions. In contrast, SA deoxygenation over Pd/SiO2 occurred primarily via decarbonylation and at a much slower rate. Pd/Al2O3 exhibited high initial SA decarboxylation activity but deactivated under the test conditions. Similar CO2 selectivity patterns among the catalysts were observed for deoxygenation of lauric and capric acids; however, the initial decarboxylation rates tended to be lower for these substrates. The influence of alkyl chain length on deoxygenation kinetics was investigated for a homologous series of C-10-C-18 fattyacids using the Pd/C catalyst. As fattyacid carbon number decreases, reaction time and H-2 consumption increase, and CO2 selectivity and initial decarboxylation rate decrease. The increase in initial decarboxylation rates for longer chain fattyacids is attributed to their greater propensity for adsorption on the activated carbon support.

Virus envelope was isolated from Plodia interpunctella granulosis virus, produced in early fourth-instar larvae. Both polar and neutral lipids were analyzed by two-dimensional thin-layer chromatography. Fattyacid composition of various individual neutral and polar lipids was determined by gas-liquid chromatography. The major components of envelope neutral lipid were diacylglycerols. Palmitic acid and stearic acid were the major saturated fattyacids in both polar and neutral lipids. Whereas palmitoleic acid was the major unsaturated fattyacids in neutral lipids, oleic acid was the major unsaturated fattyacid in the polar lipids.

Objectives Excess fat in the diet can impact neuropsychiatric functions by negatively affecting cognition, mood and anxiety. We sought to show that the free fattyacid (FFA), palmitic acid, can cause adverse biobehaviors in mice that lasts beyond an acute elevation in plasma FFAs. Methods Mice were administered palmitic acid or vehicle as a single intraperitoneal (IP) injection. Biobehaviors were profiled 2 and 24 hrs after palmitic acid treatment. Quantification of dopamine (DA), norepinephrine (NE), serotonin (5-HT) and their major metabolites was performed in cortex, hippocampus and amygdala. FFA concentration was determined in plasma. Relative fold change in mRNA expression of unfolded protein response (UPR)-associated genes was determined in brain regions. Results In a dose-dependent fashion, palmitic acid rapidly reduced mouse locomotor activity by a mechanism that did not rely on TLR4, MyD88, IL-1, IL-6 or TNFα but was dependent on fattyacid chain length. Twenty-four hrs after palmitic acid administration mice exhibited anxiety-like behavior without impairment in locomotion, food intake, depressive-like behavior or spatial memory. Additionally, the serotonin metabolite 5-HIAA was increased by 33% in the amygdala 24 hrs after palmitic acid treatment. Conclusions Palmitic acid induces anxiety-like behavior in mice while increasing amygdala-based serotonin metabolism. These effects occur at a time point when plasma FFA levels are no longer elevated. PMID:25016520

Hypochlorous acid treatment of a microalga, Chlorella vulgaris, was investigated to improve the quality of microalgal lipid and to obtain high biodiesel-conversion yield. Because chlorophyll deactivates the catalyst for biodiesel conversion, its removal in the lipid-extraction step enhances biodiesel productivity. When microalgae contacted the hypochlorous acid, chlorophyll was removed, and resultant changes in fattyacid composition of microalgal lipid were observed. The lipid-extraction yield after activated clay treatment was 32.7 mg lipid/g cell; after NaClO treatment at 0.8% available chlorine concentration, it was 95.2 mg lipid/g cell; and after NaCl electrolysis treatment at the 1 g/L cell concentration, it was 102.4 mg lipid/g cell. While the contents of all of the unsaturated fattyacids except oleic acid, in the microalgal lipid, decreased as the result of NaClO treatment, the contents of all of the unsaturated fattyacids including oleic acid decreased as the result of NaCl electrolysis treatment.

It has been recognized that human hair lipids play crucial roles in the integrity of cells and matrices, while the details of distribution and structure of the minor lipids are hardly known. Here we investigated the lipids at the hair surface, at the interface between cuticle and cortex and in the interior of hair (cortex, medulla and melanin granules). Hair lipids and fattyacids and their metabolites were detected and characterized by using infrared spectroscopy and several mass spectrometry techniques (FTIR, ToF-SIMS, GCMS, and ESI-MS). As a result, it was found that unsaturated fattyacids were present more in the cortex of hair than at the hair surface. At the interface between cuticle and cortex, it is suggested that steryl glycoside-like lipids containing N-acetylglucosamine were present, and contributing to the adhesion between the cuticle and cortex of hair. Oxidative metabolites derived from integral fattyacids such as linoleic and alpha-linolenic acids were found in the hair bulb and melanin granules. Especially the oxidative metabolites of alpha-linolenic acid were integrated into the lipids non-covalently and tightly bound to melanin granules (namely, melanin lipids) and suggested as being involved in the biosynthetic processes of melanosome.

Lipid-correlated disease such as atherosclerosis has been an important medical research topic for decades. Many new microscopic imaging techniques such as coherent anti-Stokes Raman scattering and third-harmonic generation (THG) microscopy were verified to have the capability to target lipids in vivo. In the case of THG microscopy, biological cell membranes and lipid bodies in cells and tissues have been shown as good sources of contrast with a laser excitation wavelength around 1200 nm. We report the THG excitation spectroscopy study of two pure free fattyacids including oleic acid and linoleic acid from 1090 to 1330 nm. Different pure fattyacids presented slightly-different THG χ(3) spectra. The measured peak values of THG third-order susceptibility χ(3) in both fattyacids were surprisingly found not to match completely with the resonant absorption wavelengths around 1190 to 1210 nm, suggesting possible wavelengths selection for enhanced THG imaging of lipids while avoiding laser light absorption. Along with the recent advancement in THG imaging, this new window between 1240 to 1290 nm may offer tremendous new opportunities for sensitive label-free lipid imaging in biological tissues.

Phytanic acid is a multibranched fattyacid with reported retinoid X receptor (RXR) and peroxisome proliferator-activated receptor-alpha (PPAR-alpha) agonist activity, which have been suggested to have preventive effects on metabolic dysfunctions. Serum level in man is strongly correlated to the intake of red meat and dairy products and the concentration in these products is strongly correlated to the chlorophyll content in the feed of the cattle. Available data suggest that phytanic acid is a natural agonist for RXR at physiological concentrations, while it is more likely that it is the metabolite pristanic acid, rather than phytanic acid itself, that acts as PPAR-alpha agonist. Animal studies show increased expression of genes involved in fattyacid oxidation, after intake of phytol, the metabolic precursor of phytanic acid, but it is at present not possible to deduce whether phytanic acid is useful in the prevention of ectopic lipid deposition. Phytanic acid is an efficient inducer of the expression of uncoupler protein 1 (UCP1). UCP1 is expressed in human skeletal muscles, were it might be important for the total energy balance. Therefore, phytanic acid may be able to stimulate energy dissipation in skeletal muscles. Phytanic acid levels in serum are associated with an increased risk of developing prostate cancer, but the available data do not support a general causal link between circulating phytanic acid and prostate cancer risk. However, certain individuals, with specific single-nucleotide polymorphisms in the gene for the enzyme alpha-methylacyl-CoA racemase, might be susceptible to raised phytanic acid levels.

Omega-3 fattyacids eicosapentaenoic acid (EPA) and docohexaenoic acid (DHA), provide significant health benefits for brain function/development and cardiovascular conditions. However, most EPA and DHA for human consumption is sourced from small fatty fish caught in coastal waters and, with depleting global fish stocks, recent research has been directed towards more sustainable sources. These include aquaculture with plant-based feeds, krill, marine microalgae, microalgae-like protists and genetically-modified plants. To meet the increasing demand for EPA and DHA, further developments are needed towards land-based sources. In particular large-scale cultivation of microalgae and plants is likely to become a reality with expected reductions in production costs, yield increasese and the adequate addressing of genetically modified food acceptance issues.

In the course of our investigations of new sources of higher plant lipids, seed fattyacid compositions and the tocochromanol contents of Salvia bracteata, S. euphratica var. euphratica, S. aucherii var. canascens, S. cryptantha, S. staminea, S. limbata, S. virgata, S. hypargeia, S. halophylla, S. syriaca and S. cilicica were investigated using GLC and HPLC systems. Some of the species are endemic to Turkey. All the Salvia sp. showed the same pattern of fattyacids. Linoleic, linolenic and oleic acid were found as the abundant components. Tocochromanol derivatives of the seed oil showed differences between Salvia species. gamma-Tocopherol was the abundant component in most of the seed oils except of S. cilicica. The total tocopherol contents of the seed oils were determined to be more than the total of tocotrienols.

The role of serum fattyacid composition in neonatal jaundice was studied by comparing the incidence of jaundice among 332 newborn infants receiving breast milk from mothers on a diet with either a low (0.1, n = 145) or a high (1.5, n = 187) polyunsaturated to saturated fattyacid (P/S) ratio. The diet was started immediately after delivery. The composition of fattyacids in the breast milk and sera of the mothers and in the sera of the newborns was evaluated from a random sample of 15 mother-newborn pairs on the control diet (low P/S ratio) and 19 pairs on the experimental diet. Five days after delivery the relative amounts of fattyacids, especially that of linoleate, in the sera of the mothers differed significantly depending on the diet. Differences were also observed in breast milk samples taken three, four or five days after delivery and in the sera of the newborns sampled at the age of four or five days. Nine of the 145 newborn infants (6.2%) in the control group had to be treated with light therapy compared with 12 out of 187 (6.4%) of the newborn infants in the experimental group (high P/S ratio). Serum bilirubin concentrations were 142.5 mumol/l (SD 65.8) and 140.7 mumol/l (SD 73.5) in the experimental and control groups, respectively, at the age of five days. It appears that the changes in the composition of serum fattyacids reached in this study had no effect on the neonatal jaundice.

Plants in the Santalaceae family, including the native cherry Exocarpos cupressiformis and sweet quandong Santalum acuminatum, accumulate ximenynic acid (trans-11-octadecen-9-ynoic acid) in their seed oil and conjugated polyacetylenic fattyacids in root tissue. Twelve full-length genes coding for microsomal Δ12 fattyacid desaturases (FADs) from the two Santalaceae species were identified by degenerate PCR. Phylogenetic analysis of the predicted amino acid sequences placed five Santalaceae FADs with Δ12 FADs, which include Arabidopsis thaliana FAD2. When expressed in yeast, the major activity of these genes was Δ12 desaturation of oleic acid, but unusual activities were also observed: i.e. Δ15 desaturation of linoleic acid as well as trans-Δ12 and trans-Δ11 desaturations of stearolic acid (9-octadecynoic acid). The trans-12-octadecen-9-ynoic acid product was also detected in quandong seed oil. The two other FAD groups (FADX and FADY) were present in both species; in a phylogenetic tree of microsomal FAD enzymes, FADX and FADY formed a unique clade, suggesting that are highly divergent. The FADX group enzymes had no detectable Δ12 FAD activity but instead catalyzed cis-Δ13 desaturation of stearolic acid when expressed in yeast. No products were detected for the FADY group when expressed recombinantly. Quantitative PCR analysis showed that the FADY genes were expressed in leaf rather than developing seed of the native cherry. FADs with promiscuous and unique activities have been identified in Santalaceae and explain the origin of some of the unusual lipids found in this plant family. PMID:24062307

Harmful algal blooms (HABs) expose aquatic organisms to multiple physical and chemical stressors during an acute time period. Algal toxins themselves may be altered by water chemistry parameters affecting their bioavailability and resultant toxicity. The purpose of this study was to determine the effects of two abiotic parameters (pH, inorganic metal salts) on the toxicity of fattyacid amides and fattyacids, two classes of lipids produced by harmful algae, including the golden alga, Prymnesium parvum, that are toxic to aquatic organisms. Rainbow trout gill cells were used as a model of the fish gill and exposed to single compounds and mixtures of compounds along with variations in pH level and concentration of inorganic metal salts. We employed artificial neural networks (ANNs) and standard ANOVA statistical analysis to examine and predict the effects of these abiotic parameters on the toxicity of fattyacid amides and fattyacids. Our results demonstrate that increasing pH levels increases the toxicity of fattyacid amides and inhibits the toxicity of fattyacids. This phenomenon is reversed at lower pH levels. Exposing gill cells to complex mixtures of chemical factors resulted in dramatic increases in toxicity compared to tests of single compounds for both the fattyacid amides and fattyacids. These findings highlight the potential of physicochemical factors to affect the toxicity of chemicals released during algal blooms and demonstrate drastic differences in the effect of pH on fattyacid amides and fattyacids.

Interrelated effects of γ-linolenic acid (GLA) and sesamin, a sesame lignan, on hepatic fattyacid synthesis and oxidation were examined. Rats were fed experimental diets supplemented with 0 or 2 g/kg sesamin (1:1 mixture of sesamin and episesamin) and containing 100 g/kg of palm oil (saturated fat), safflower oil rich in linoleic acid, or oil of evening primrose origin containing 43% GLA (GLA oil) for 18 days. In rats fed sesamin-free diets, GLA oil, compared with other oils, increased the activity and mRNA levels of various enzymes involved in fattyacid oxidation, except for some instances. Sesamin greatly increased these parameters, and the enhancing effects of sesamin on peroxisomal fattyacid oxidation rate and acyl-CoA oxidase, enoyl-CoA hydratase and acyl-CoA thioesterase activities were more exaggerated in rats fed GLA oil than in the animals fed other oils. The combination of sesamin and GLA oil also synergistically increased the mRNA levels of some peroxisomal fattyacid oxidation enzymes and of several enzymes involved in fattyacid metabolism located in other cell organelles. In the groups fed sesamin-free diets, GLA oil, compared with other oils, markedly reduced the activity and mRNA levels of various lipogenic enzymes. Sesamin reduced all these parameters, except for malic enzyme, in rats fed palm and safflower oils, but the effects were attenuated in the animals fed GLA oil. These changes by sesamin and fat type accompanied profound alterations in serum lipid levels. This may be ascribable to the changes in apolipoprotein-B-containing lipoproteins.

Erythrocyte membrane fattyacids (FA), such as oleic acid, are related to acute coronary syndrome. There is no report about the effect of omega-3 FA on oleic acid in peritoneal dialysis (PD) patients. We hypothesized that omega-3 FA can modify erythrocyte membrane FA, including oleic acid, in PD patients. In a double-blind, randomized, placebo-controlled study, 18 patients who were treated with PD for at least 6 months were randomized to treatment for 12 weeks with omega-3 FA or placebo. Erythrocyte membrane FA content was measured by gas chromatography at baseline and after 12 weeks. The erythrocyte membrane content of eicosapentaenoic acid and docosahexaenoic acid was significantly increased and saturated FA and oleic acid were significantly decreased in the omega-3 FA supplementation group after 12 weeks compared to baseline. In conclusion, erythrocyte membrane FA content, including oleic acid, was significantly modified by omega-3 FA supplementation for 12 weeks in PD patients.

Context: A portion of free fattyacids (FFA) released from adipose tissue lipolysis are re-stored in adipocytes via direct uptake. Rates of direct adipose tissue FFA storage are much greater in women than men, but women also have greater systemic FFA flux and more body fat. Objective: We tested the hypotheses that experimental increases in FFA in men would equalize the rates of direct adipose tissue FFA storage in men and women. Design: We used a lipid emulsion infusion to raise FFA in men to levels seen in post-absorptive women. Direct FFA storage (μmol·kg fat−1·min−1) rates in abdominal and femoral fat was assessed using stable isotope tracer infusions to measure FFA disappearance rates and an iv FFA radiotracer bolus/timed biopsy. Setting: These studies were performed in a Clinical Research Center. Participants: Data from 13 non-obese women was compared with that from eight obese and eight non-obese men. Intervention: The men received a lipid emulsion infusion to raise FFA. Main Outcome Measures: We measured the rates of direct FFA storage in abdominal and femoral adipose tissue. Results: The three groups were similar in age and FFA flux by design; obese men had similar body fat percentage as non-obese women. Despite matching for FFA concentrations and flux, FFA storage per kg abdominal (P < .01) and femoral (P < .001) fat was less in both lean and obese men than in non-obese women. Abdominal FFA storage rates were correlated with proteins/enzymes in the FFA uptake/triglyceride synthesis pathway in men. Conclusion: The lesser rates of direct FFA adipose tissue in men compared with women cannot be explained by reduced FFA availability. PMID:25192251

Variations in plasma fattyacid (FA) concentrations are detected by FA sensing neurons in specific brain areas such as the hypothalamus. These neurons play a physiological role in the control of food intake and the regulation of hepatic glucose production. Le Foll et al. previously showed in vitro that at least 50% of the FA sensing in ventromedial hypothalamic (VMH) neurons is attributable to the interaction of long chain FA with FA translocase/CD36 (CD36). The present work assessed whether in vivo effects of hypothalamic FA sensing might be partly mediated by CD36 or intracellular events such as acylCoA synthesis or β-oxidation. To that end, a catheter was implanted in the carotid artery toward the brain in male Wistar rats. After 1 wk recovery, animals were food-deprived for 5 h, then 10 min infusions of triglyceride emulsion, Intralipid +/− heparin (IL, ILH, respectively) or saline/heparin (SH) were carried out and food intake was assessed over the next 5 h. Experimental groups included: 1) Rats previously injected in ventromedian nucleus (VMN) with shRNA against CD36 or scrambled RNA; 2) Etomoxir (CPT1 inhibitor) or saline co-infused with ILH/SH; and 3) Triacsin C (acylCoA synthase inhibitor) or saline co-infused with ILH/SH. ILH significantly lowered food intake during refeeding compared to SH (p<0.001). Five hours after refeeding, etomoxir did not affect this inhibitory effect of ILH on food intake while VMN CD36 depletion totally prevented it. Triacsin C also prevented ILH effects on food intake. In conclusion, the effect of FA to inhibit food intake is dependent on VMN CD36 and acylCoA synthesis but does not required FA oxidation. PMID:24040150

Several studies have reported that lactic acid bacteria may increase the production of free fattyacids by lipolysis of milk fat, though no studies have been found in the literature showing the effect of kefir grains on the composition of fattyacids in milk. In this study the influence of kefir grains from different origins [Rio de Janeiro (AR), Viçosa (AV) e Lavras (AD)], different time of storage, and different fat content on the fattyacid content of cow milk after fermentation was investigated. Fattyacid composition was determined by gas chromatography. Values were considered significantly different when p<0.05. The highest palmitic acid content, which is antimutagenic compost, was seen in AV grain (36.6g/100g fattyacids), which may have contributed to increasing the antimutagenic potential in fermented milk. Higher monounsaturated fattyacid (25.8g/100g fattyacids) and lower saturated fattyacid (72.7g/100g fattyacids) contents were observed in AV, when compared to other grains, due to higher Δ9-desaturase activity (0.31) that improves the nutritional quality of lipids. Higher oleic acid (25.0g/100g fattyacids) and monounsaturated fattyacid (28.2g/100g fattyacids) and lower saturated fattyacid (67.2g/100g fattyacids) contents were found in stored kefir relatively to fermented kefir leading to possible increase of antimutagenic and anticarcinogenic potential and improvement of nutritional quality of lipids in storage milk. Only high-lipidic matrix displayed increase polyunsaturated fattyacids after fermentation. These findings open up new areas of study related to optimizing desaturase activity during fermentation in order to obtaining a fermented product with higher nutritional lipid quality. PMID:26444286

Fattyacid-derived biofuels can be a better solution than bioethanol to replace petroleum fuel, since they have similar energy content and combustion properties as current transportation fuels. The environmentally friendly microbial fermentation process has been used to synthesize advanced biofuels from renewable feedstock. Due to their robustness as well as the high tolerance to fermentation inhibitors and phage contamination, yeast strains such as Saccharomyces cerevisiae and Yarrowia lipolytica have attracted tremendous attention in recent studies regarding the production of fattyacid-derived biofuels, including fattyacids, fattyacid ethyl esters, fatty alcohols, and fatty alkanes. However, the native yeast strains cannot produce fattyacids and fattyacid-derived biofuels in large quantities. To this end, we have summarized recent publications in this review on metabolic engineering of yeast strains to improve the production of fattyacid-derived biofuels, identified the bottlenecks that limit the productivity of biofuels, and categorized the appropriate approaches to overcome these obstacles. PMID:26106371

This investigation studied the efficiency of high performance liquid chromatography in the determination of free fattyacids present on the...utilized to eliminate the microbial contamination. The high performance liquid chromatography provided excellent separation of skin fattyacids for

A method is described for the determination of fattyacids in dried sweat spot and plasma samples using gas chromatography with flame ionization detection. Plasma and dried sweat spot samples were obtained from a group of blood donors. The sweat was collected from each volunteer during exercise. Sweat was spotted onto collection paper containing butylated hydroxytoluene. Fattyacids were derivatized with acetyl chloride in methanol to form methyl esters of fattyacids. The fattyacids in dried sweat spot samples treated with butylated hydroxytoluene and stored at -20°C were stable for 3 months. Our results indicate that sweat contains, among fattyacids with short chain, also fattyacids with long chain and unsaturated fattyacids. Linear relationships between percentage content of selected fattyacids in dried sweat spot and plasma were observed.

Human skin fattyacids are a potent aspect of our innate defenses, giving surface protection against potentially invasive organisms. They provide an important parameter in determining the ecology of the skin microflora, and alterations can lead to increased colonization by pathogens such as Staphylococcus aureus. Harnessing skin fattyacids may also give a new avenue of exploration in the generation of control measures against drug-resistant organisms. Despite their importance, the mechanism(s) whereby skin fattyacids kill bacteria has remained largely elusive. Here, we describe an analysis of the bactericidal effects of the major human skin fattyacid cis-6-hexadecenoic acid (C6H) on the human commensal and pathogen S. aureus. Several C6H concentration-dependent mechanisms were found. At high concentrations, C6H swiftly kills cells associated with a general loss of membrane integrity. However, C6H still kills at lower concentrations, acting through disruption of the proton motive force, an increase in membrane fluidity, and its effects on electron transfer. The design of analogues with altered bactericidal effects has begun to determine the structural constraints on activity and paves the way for the rational design of new antistaphylococcal agents.

Many studies with conjugated linoleic acid (CLA) indicate that it has a protective effect against mammary cancer. Because dairy products are the most important dietary sources of CLA, we have investigated the CLA concentrations and additionally the fattyacid profiles and chemical composition of several commercial, traditional, Greek yogurts from different geographical origin. The fat content of yogurts was in the order of goatfatty acids (SFA) were found in low-fat yogurts, of monounsaturated fattyacids (MUFA) in sheep milk yogurts and of polyunsaturated fattyacid (PUFA) in low-fat cow milk yogurts.

To assess whether ursodeoxycholic acid (UDCA) treatment has any beneficial effect on essential fattyacid (EFA) deficiency in patients who have had a Kasai operation for extrahepatic atresia (EBA), responses of serum fattyacids to UDCA administration (15 mg/kg/d) were investigated in eight jaundice-free patients and in eight patients with jaundice (serum total bilirubin > or = 1.0 mg/dL). All patients were also given taurine supplementation (100 mg/kg/d). Serum fattyacid composition was determined before and 6 months after UDCA treatment. Serum total bile acid concentration and serum total bilirubin value, as a part of conventional liver function tests, were measured before and during UDCA therapy. Before UDCA treatment, the concentrations of linoleic acid and arachidonic acid were significantly lower (P > .05 for the former; P > .01 for the latter) in both the jaundice and jaundice-free groups than in the controls. After 6 months of treatment, the linoleic acid concentration significantly increased (P > .05), to the normal range, in the jaundice-free group, but not in the jaundice group. The arachidonic acid concentration did not increase significantly in either group. The serum total bile acid concentration was lower in six of the eight jaundice-free patients and in four of the eight jaundice patients. The serum total bilirubin value decreased in six of the eight jaundice-free patients and in four of the eight jaundice patients; however, the degree of improvement was not statistically significant in either group. No side effects developed, and there were no changes in blood chemistry values unrelated to liver disease.(ABSTRACT TRUNCATED AT 250 WORDS)

Microbial biosynthesis of fattyacid-derived biofuels from renewable carbon sources has attracted significant attention in recent years. Free fattyacids (FFAs) can be used as precursors for the production of micro-diesel. The expression of codon optimized two plants (Umbellularia californica and Cinnamomum camphora) medium-chain acyl-acyl carrier protein (ACP) thioesterase genes (ucFatB and ccFatB) in Escherichia coli resulted in a very high level of extractable medium-chain-specific hydrolytic activity and caused large accumulation of medium-chain free fattyacids. By heterologous co-expression of acyl-coenzyme A:diacylglycerol acyltransferase from Acinetobacter baylyi ADP1, specific plant thioesterases in E. coli, with supplementation of exogenous ethanol, resulted in drastic changes in fattyacid ethyl esters (FAEEs) composition ranging from 12:0 to 18:1. Through an optimized microbial shake-flask fermentation of two modified E. coli strains, yielded FFAs and FAEEs in the concentration of approximately 500 mg L(-1)/250 mg L(-1) and 2.01 mg g(-1)/1.99 mg g(-1), respectively. The optimal ethanol level for FAEEs yield in the two recombinant strains was reached at the 3% ethanol concentration, which was about 5.4-fold and 1.93-fold higher than that of 1% ethanol concentration.

Peanut, a high-oil crop with about 50% oil content, is either crushed for oil or used as edible products. Fattyacid composition determines the oil quality which has high relevance to consumer health, flavor, and shelf life of commercial products. In addition to the major fattyacids, oleic acid (C1...

The potential health benefit of omega-3 fattyacids has been the focus of much research in the past decade. While the typical diet in the United States has a much greater ratio of omega-6 fattyacids compared with omega-3 fattyacids, research is showing that shifting this ratio-by increased consumption of fatty fish or fish oil supplements-may provide significant health benefits. Reductions in cardiovascular risk, depression, and rheumatoid arthritis symptoms have been correlated with omega-3 fattyacid intake, and there is increased interest in the use of omega-3 fattyacid supplementation for other psychiatric illnesses and prevention of Alzheimer's disease.

While intakes of the omega-3 fattyacid α-linolenic acid (ALA) are similar in vegetarians and non-vegetarians, intakes of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are low in vegetarians and virtually absent in vegans. Plasma, blood and tissue levels of EPA and DHA are lower in vegetarians than in non-vegetarians, although the clinical significance of this is unknown. Vegetarians do not exhibit clinical signs of DHA deficiency, but further research is required to ascertain whether levels observed in vegetarians are sufficient to support optimal health. ALA is endogenously converted to EPA and DHA, but the process is slow and inefficient and is affected by genetics, sex, age and dietary composition. Vegetarians can take practical steps to optimise conversion of ALA to EPA and DHA, including reducing intake of linoleic acid. There are no official separate recommendations for intake of fattyacids by vegetarians. However, we suggest that vegetarians double the current adequate intake of ALA if no direct sources of EPA and DHA are consumed. Vegetarians with increased needs or reduced conversion ability may receive some advantage from DHA and EPA supplements derived from microalgae. A supplement of 200-300 mg/day of DHA and EPA is suggested for those with increased needs, such as pregnant and lactating women, and those with reduced conversion ability, such as older people or those who have chronic disease (eg, diabetes).

In the sport field, non-esterified fattyacids (NEFA) are important for the physical performance during the aerobic exercise of short intensity and long duration. In man, rat, goat and in the sedentary horse studies on the chronometabolism showed the presence of a circadian rhythm of the plasmatic concentration of NEFA while data for the athletic horse are lacking. To define a chronogram helpful for a specific planning and the differentiation of the training programmme in the athletic horse, the circadian pattern of some fattyacids (NEFA, palmitic, stearic, oleic, linoleic and linolenic acids) was studied in five Sella Italiana horses. These horses trained following a daily model of activity consisting of walk, trot, gallop and jump of obstacles of different heights. Blood samples were collected from the jugular vein every 4 h, starting at 08:00 hours, for 2 days to assess the concentrations of total NEFA (by spectrophotometry), palmitic, stearic, oleic, linoleic and linolenic acids (by gas chromatography). anova for repeated measures showed a statistical significant effect of the time of the day in NEFA, oleic and linolenic acids. The application of the periodic model showed the periodic pattern of NEFA, oleic, linoleic and linolenic acids. Acrophases were in the afternoon for all parameters. The results obtained showed a different trend of the circadian pattern of the studied parameters in the athletic horse than in the sedentary one because the physical activity and the post-prandial metabolism acted as zeitgebers.

This research has determined qualitatively and quantitatively the fattyacids composition of white (Morus alba) and black (Morus nigra) fruits grown in Spain, in 2013 and 2014. Four clones of each species were studied. Fourteen fattyacids were identified and quantified in mulberry fruits. The most abundant fattyacids were linoleic (C18:2), palmitic (C16:0), oleic (C18:1), and stearic (C18:0) acids in both species. The main fattyacid in all clones was linoleic (C18:2), that ranged from 69.66% (MN2) to 78.02% (MA1) of the total fattyacid content; consequently Spanish mulberry fruits were found to be rich in linoleic acid, which is an essential fattyacid. The fattyacid composition of mulberries highlights the nutritional and health benefits of their consumption.

Branched-chain fattyacids of the iso and anteiso series occur in many bacteria as the major acyl constituents of membrane lipids. In addition, omega-cyclohexyl and omega-cycloheptyl fattyacids are present in several bacterial species. These two types of fattyacids are synthesized by the repeated condensation of malonyl coenzyme A with one of the branched-chain and cyclic primers by the same enzyme system. The pathway of de novo branched-chain fattyacid synthesis differs only in initial steps of synthesis from that of the common straight-chain fattyacid (palmitic acid) present in most organisms. The cell membranes composed largely of iso-, anteiso-, and omega-alicyclic acids support growth of bacteria, which inhabit normal as well as extreme environments. The occurrence of these types of fattyacids as major cellular fattyacids is an important criterion used to aid identification and classification of bacteria. PMID:1886522

The physical properties in water of a series of 1:1 acid-soap compounds formed from fattyacids and potassium soaps with saturated (10-18 carbons) and omega-9 monounsaturated (18 carbons) hydrocarbon chains have been studied by using differential scanning calorimetry (DSC), X-ray diffraction, and direct and polarized light microscopy. DSC showed three phase transitions corresponding to the melting of crystalline water, the melting of crystalline lipid hydrocarbon chains, and the decomposition of the 1:1 acid-soap compound into its parent fattyacid and soap. Low- and wide-angle X-ray diffraction patterns revealed spacings that corresponded (with increasing hydration) to acid-soap crystals, hexagonal type II liquid crystals, and lamellar liquid crystals. The lamellar phase swelled from bilayer repeat distances of 68 (at 45% H2O) to 303 A (at 90% H2O). Direct and polarized light micrographs demonstrated the formation of myelin figures as well as birefringent optical textures corresponding to hexagonal and lamellar mesophases. Assuming that 1:1 potassium hydrogen dioleate and water were two components, we constructed a temperature-composition phase diagram. Interpretation of the data using the Gibbs phase rule showed that, at greater than 30% water, hydrocarbon chain melting was accompanied by decomposition of the 1:1 acid-soap compound and the system changed from a two-component to a three-component system. Comparison of hydrated 1:1 fattyacid/soap systems with hydrated soap systems suggests that the reduced degree of charge repulsion between polar groups causes half-ionized fattyacids in excess water to form bilayers rather than micelles.(ABSTRACT TRUNCATED AT 250 WORDS)

A recent meta-analysis by Chowdhury et al. (2014) has disclaimed the association between coronary artery diseases and either circulating blood levels or the intake of total saturated fattyacids (SFA). Scrutiny revealed that two of the eight studies included in the meta-analysis focused on the proportion of pentadecanoic acid (C15:0) and heptadecanoic acid (C17:0) and their impact on cardiovascular disease (CVD) risk. These odd-chain fattyacids are markers for milk or ruminant fat intake. Both studies indicated inverse associations between milk-fat intake and first-ever myocardial infarction. Neither of the two studies described the association between total circulating blood SFA on coronary outcomes. In contrast to the cardioprotective effects of dairy consumption, we expected that an elevated intake of palmitic acid (C16:0) and stearic acid (C18:0) de novo may raise CVD risk. Thus, it is of particular importance to differentiate the effects of individual circulating SFA on cardiovascular outcomes. Excluding the studies that evaluated the association of fattyacids from milk fat and cardiovascular outcomes revealed a positive association of total SFA blood levels and coronary outcome (RR 1.21, CI 1.04-1.40). Therefore, results obtained from studies of C15:0 and C17:0 cannot be mixed with results from studies of other SFA because of the opposite physiological effects of regular consumption of foods rich in C16:0 and C18:0 compared to high intake of milk or ruminant fat. In our opinion, it is vital to analyze the impact of individual SFA on CVD incidence in order to draw prudent conclusions.

In order to establish Ciona intestinalis as a new bioresource for n-3 fattyacids-rich marine lipids, the animal was fractionated into tunic and inner body tissues prior to lipid extraction. The lipids obtained were further classified into neutral lipids (NL), glycolipids (GL) and phospholipids (PL) followed by qualitative and quantitative analysis using GC-FID, GC-MS, (1)H NMR, 2D NMR, MALDI-TOF-MS and LC-ESI-MS methods. It was found that the tunic and inner body tissues contained 3.42-4.08% and 15.9-23.4% of lipids respectively. PL was the dominant lipid class (42-60%) irrespective of the anatomic fractions. From all lipid fractions and classes, the major fattyacids were 16:0, 18:1n-9, C20:1n-9, C20:5n-3 (EPA) and C22:6n-3 (DHA). The highest amounts of long chain n-3 fattyacids, mainly EPA and DHA, were located in PL from both body fractions. Cholestanol and cholesterol were the dominant sterols together with noticeable amounts of stellasterol, 22 (Z)-dehydrocholesterol and lathosterol. Several other identified and two yet unidentified sterols were observed for the first time from C. intestinalis. Different molecular species of phosphatidylcholine (34 species), sphingomyelin (2 species), phosphatidylethanolamine (2 species), phosphatidylserine (10 species), phosphatidylglycerol (9 species), ceramide (38 species) and lysophospholipid (5 species) were identified, representing the most systematic PL profiling knowledge so far for the animal. It could be concluded that C. intestinalis lipids should be a good alternative for fish oil with high contents of n-3 fattyacids. The lipids would be more bioavailable due to the presence of the fattyacids being mainly in the form of PL.

The importance of Omega-3 fattyacids intake from dietary supplements or from food sources (mainly fish) has recently become "common knowledge" in the mass media as well as in popular science magazines and advertisements. Therefore, the authors wish to review the updated evidence-based literature regarding the relationship between Omega-3 fattyacid intake and morbidity and its preventative effects in cardiovascular, bone, kidney autoimmune, GI tract diseases, CNS and mental diseases, cancer, diabetes, asthma, ophthalmological health, organ transplants and child and maternal health. Recommendations regarding optimal intake of these fattyacids throughout the lifecycle by various health authorities are cited. The conclusion presents the authors' recommendations for optimal Omega-3 intake in Israel: Recommendations for the general population is to consume at least two weekly portions of fatty fish. For patients with hypertriglyceridemia, dietary supplements containing fish oil, in addition to the above diet, can be considered to be part of the complete medical treatment and follow-up. Limiting fish consumption in risk group populations, such as pregnant women, will also be considered.

Proximate composition, fattyacid analysis and protein digestibility-corrected amino acid score (PDCAAS) in three commercially important cephalopods of the Mediterranean sea (cuttlefish, octopus and squid) were determined. The results of the proximate analysis showed that these species had very high protein:fat ratios similar to lean beef. Docosahexaenoic, palmitic and eicosipentaenoic acid were the most abundant fattyacids among analyzed species. The amount of n-3 fattyacids was higher than that of saturated, monounsaturated and n-6 fattyacids. Despite the fact that cephalopods contain small amounts of fat they were found quite rich in n-3 fattyacids. Finally, PDCAAS indicated that these organisms had a very good protein quality.

AIM: To investigate how the saturated and unsaturated fattyacid composition influences the susceptibility of developing acute pancreatitis. METHODS: Primary pancreatic acinar cells were treated with low and high concentrations of different saturated and unsaturated fattyacids, and changes in the cytosolic Ca2+ signal and the expression of protein kinase C (PKC) were measured after treatment. RESULTS: Unsaturated fattyacids at high concentrations, including oleic acid, linoleic acid, palmitoleic acid, docosahexaenoic acid, and arachidonic acid, induced a persistent rise in cytosolic Ca2+ concentrations in acinar cells. Unsaturated fattyacids at low concentrations and saturated fattyacids, including palmitic acid, stearic acid, and triglycerides, at low and high concentrations were unable to induce a rise in Ca2+ concentrations in acinar cells. Unsaturated fattyacids at high concentrations but not saturated fattyacids induced intra-acinar cell trypsin activation and cell damage and increased PKC expression. CONCLUSION: At sufficiently high concentrations, unsaturated fattyacids were able to induce acinar cells injury and promote the development of pancreatitis. Unsaturated fattyacids may play a distinctive role in the pathogenesis of pancreatitis through the activation of PKC family members. PMID:26327761

Ricinoleate, a monohydroxy fattyacid, in castor oil has many industrial uses. Dihydroxy fattyacids can also be used in industry. The C18 HPLC fractions of castor oil were used for mass spectrometry of lithium addicts to identify the acylglycerols containing dihydroxy fattyacids. Four diacylglycer...

Modifications in the USDA National Nutrient Databank System have facilitated the Nutrient Data Laboratory (NDL) in upgrading fattyacid handling. High priority was given to enabling fattyacid data to be entered in units as received (e.g. percent methyl esters, percent fattyacid of total fat) and t...

The synthesis of fattyacids is an essential primary metabolic process for energy storage and cellular structural integrity. Assembly of saturated fattyacids is achieved by fattyacid synthases (FASs) that combine acetyl- and malonyl-CoAs by repetitive decarboxylative Claisen condensations with su...

Toll-like receptor 4 (TLR4) and TLR2 were shown to be activated by saturated fattyacids (SFAs) but inhibited by docosahexaenoic acid (DHA). However, one report suggested that SFA-induced TLR activation in cell culture systems is due to contaminants in BSA used for solubilizing fattyacids. This report raised doubt about proinflammatory effects of SFAs. Our studies herein demonstrate that sodium palmitate (C16:0) or laurate (C12:0) without BSA solubilization induced phosphorylation of inhibitor of nuclear factor-κB α, c-Jun N-terminal kinase (JNK), p44/42 mitogen-activated-kinase (ERK), and nuclear factor-κB subunit p65, and TLR target gene expression in THP1 monocytes or RAW264.7 macrophages, respectively, when cultured in low FBS (0.25%) medium. C12:0 induced NFκB activation through TLR2 dimerized with TLR1 or TLR6, and through TLR4. Because BSA was not used in these experiments, contaminants in BSA have no relevance. Unlike in suspension cells (THP-1), BSA-solubilized C16:0 instead of sodium C16:0 is required to induce TLR target gene expression in adherent cells (RAW264.7). C16:0-BSA transactivated TLR2 dimerized with TLR1 or TLR6 and through TLR4 as seen with C12:0. These results and additional studies with the LPS sequester polymixin B and in MyD88(-/-) macrophages indicated that SFA-induced activation of TLR2 or TLR4 is a fattyacid-specific effect, but not due to contaminants in BSA or fattyacid preparations.

The effects of fattyacids on cancer cells have been studied for decades. The roles of dietary long-chain n-3 polyunsaturated fattyacids, and of microbiome-generated short-chain butyric acid, have been of particular interest over the years. However, the roles of free fattyacid receptors (FFARs) in mediating effects of fattyacids in tumor cells have only recently been examined. In reviewing the literature, the data obtained to date indicate that the long-chain FFARs (FFA1 and FFA4) play different roles than the short-chain FFARs (FFA2 and FFA3). Moreover, FFA1 and FFA4 can in some cases mediate opposing actions in the same cell type. Another conclusion is that different types of cancer cells respond differently to FFAR activation. Currently, the best-studied models are prostate, breast, and colon cancer. FFA1 and FFA4 agonists can inhibit proliferation and migration of prostate and breast cancer cells, but enhance growth of colon cancer cells. In contrast, FFA2 activation can in some cases inhibit proliferation of colon cancer cells. Although the available data are sometimes contradictory, there are several examples in which FFAR agonists inhibit proliferation of cancer cells. This is a unique response to GPCR activation that will benefit from a mechanistic explanation as the field progresses. The development of more selective FFAR agonists and antagonists, combined with gene knockout approaches, will be important for unraveling FFAR-mediated inhibitory effects. These inhibitory actions, mediated by druggable GPCRs, hold promise for cancer prevention and/or therapy.

A gas chromatographic with flame ionization detector (GC-MS FID) method for the identification and quantification of fattyacids based on the extraction of lipids and derivatisation of free acids to form methyl esters was developed and validated. The proposed method was evaluated to a number of standard FAs, and Bronte pistachios samples were used for that purpose and to demonstrate the applicability of the proposed method. In this regard, repeatability, mean and standard deviation of the analytical procedure were calculated. The results obtained have demonstrated oleic acid as the main component of Bronte pistachios (72.2%) followed by linoleic acid (13.4%) and showed some differences in composition with respect to Tunisian, Turkish and Iranian pistachios.

Chlorogenic acid as a natural hydroxycinnamic acid has protective effect for liver. Endotoxin induced metabolic disorder, such as lipid dysregulation and hyperlipidemia. In this study, we investigated the effect of chlorogenic acid in rats with chronic endotoxin infusion. The Sprague-Dawley rats with lipid metabolic disorder (LD group) were intraperitoneally injected endotoxin. And the rats of chlorogenic acid-LD group were daily received chlorogenic acid by intragastric administration. In chlorogenic acid-LD group, the area of visceral adipocyte was decreased and liver injury was ameliorated, as compared to LD group. In chlorogenic acid-LD group, serum triglycerides, free fattyacids, hepatic triglycerides and cholesterol were decreased, the proportion of C20:1, C24:1 and C18:3n-6, Δ9-18 and Δ6-desaturase activity index in the liver were decreased, and the proportion of C18:3n-3 acid was increased, compared to the LD group. Moreover, levels of phosphorylated AMP-activated protein kinase, carnitine palmitoyltransferase-I, and fattyacid β-oxidation were increased in chlorogenic acid-LD group compared to LD rats, whereas levels of fattyacid synthase and acetyl-CoA carboxylase were decreased. These findings demonstrate that chlorogenic acid effectively improves hepatic lipid dysregulation in rats by regulating fattyacid metabolism enzymes, stimulating AMP-activated protein kinase activation, and modulating levels of hepatic fattyacids.

The fattyacid composition of eggs is highly reflective of the diet of the laying hen; therefore, nutritionally important fattyacids can be increased in eggs in order to benefit human health. To explore the factors affecting the hen's metabolism and deposition of fattyacids of interest, the current research was divided into two studies. In Study 1, the fattyacid profile of eggs from Bovan White hens fed either 8%, 14%, 20%, or 28% of the omega-6 fattyacid, linoleic acid (LA) (expressed as a percentage of total fattyacids), and an additional treatment of 14% LA containing double the amount of saturated fat (SFA) was determined. Omega-6 fattyacids and docosapentaenoic acid (DPA) in the yolk were significantly (P < 0.05) increased, and oleic acid (OA) and eicosapentaenoic acid (EPA) were significantly decreased with an increasing dietary LA content. In Study 2, the fattyacid and sensory profiles were determined in eggs from Shaver White hens fed either (1) 15% or 30% of the omega-3 fattyacid, alpha-linolenic acid (ALA) (of total fattyacids), and (2) low (0.5), medium (1), or high (2) ratios of SFA: LA+OA. Increasing this ratio resulted in marked increases in lauric acid, ALA, EPA, DPA, and docosahexaenoic acid (DHA), with decreases in LA and arachidonic acid. Increasing the dietary ALA content from 15% to 30% (of total fattyacids) did not overcome the DHA plateau observed in the yolk. No significant differences (P ≥ 0.05) in aroma or flavor between cooked eggs from the different dietary treatments were observed among trained panelists (n = 8). The results showed that increasing the ratio of SFA: LA+OA in layer diets has a more favorable effect on the yolk fattyacid profile compared to altering the LA content at the expense of OA, all while maintaining sensory quality. PMID:24804037

The fattyacid composition of eggs is highly reflective of the diet of the laying hen; therefore, nutritionally important fattyacids can be increased in eggs in order to benefit human health. To explore the factors affecting the hen's metabolism and deposition of fattyacids of interest, the current research was divided into two studies. In Study 1, the fattyacid profile of eggs from Bovan White hens fed either 8%, 14%, 20%, or 28% of the omega-6 fattyacid, linoleic acid (LA) (expressed as a percentage of total fattyacids), and an additional treatment of 14% LA containing double the amount of saturated fat (SFA) was determined. Omega-6 fattyacids and docosapentaenoic acid (DPA) in the yolk were significantly (P < 0.05) increased, and oleic acid (OA) and eicosapentaenoic acid (EPA) were significantly decreased with an increasing dietary LA content. In Study 2, the fattyacid and sensory profiles were determined in eggs from Shaver White hens fed either (1) 15% or 30% of the omega-3 fattyacid, alpha-linolenic acid (ALA) (of total fattyacids), and (2) low (0.5), medium (1), or high (2) ratios of SFA: LA+OA. Increasing this ratio resulted in marked increases in lauric acid, ALA, EPA, DPA, and docosahexaenoic acid (DHA), with decreases in LA and arachidonic acid. Increasing the dietary ALA content from 15% to 30% (of total fattyacids) did not overcome the DHA plateau observed in the yolk. No significant differences (P ≥ 0.05) in aroma or flavor between cooked eggs from the different dietary treatments were observed among trained panelists (n = 8). The results showed that increasing the ratio of SFA: LA+OA in layer diets has a more favorable effect on the yolk fattyacid profile compared to altering the LA content at the expense of OA, all while maintaining sensory quality.

Heat and high pressure resistant strains of Escherichia coli are a challenge to food safety. This study investigated effects of cyclopropane fattyacids (CFAs) on stress tolerance in the heat- and pressure-resistant strain E. coli AW1.7 and the sensitive strain E. coli MG1655. The role of CFAs was explored by disruption of cfa coding for CFA synthase with an in-frame, unmarked deletion method. Both wild-type strains consumed all the unsaturated fattyacids (C16:1 and C18:1) that were mostly converted to CFAs and a low proportion to saturated fattyacid (C16:0). Moreover, E. coli AW1.7 contained a higher proportion of membrane C19:0 cyclopropane fattyacid than E. coli MG1655 (P<0.05). The Δcfa mutant strains did not produce CFAs, and the corresponding substrates C16:1 and C18:1 accumulated in membrane lipids. The deletion of cfa did not alter resistance to H2O2 but increased the lethality of heat, high pressure and acid treatments in E. coli AW1.7, and E. coli MG1655. E. coli AW1.7 and its Δcfa mutant were more resistant to pressure and heat but less resistant to acid stress than E. coli MG1655. Heat resistance of wild-type strains and their Δcfa mutant was also assessed in beef patties grilled to an internal temperature of 71 °C. After treatment, cell counts of wild type strains were higher than those of the Δcfa mutant strains. In conclusion, CFA synthesis in E. coli increases heat, high pressure and acid resistance, and increases heat resistance in food. This knowledge on mechanisms of stress resistance will facilitate the design of intervention methods for improved pathogen control in food production.